


I Knew You Were Trouble From The Day I Met You

by ArtemisAnne (KasMarie)



Series: Bad For Me 'Verse' [2]
Category: Supernatural
Genre: ALL THE KINKS, Anal Sex, BDSM, Bottom Castiel, Bottom Dean, Dom Castiel, Dom/sub, Enthusiastic Consent, Explicit Consent, F/F, Food Kink, I take kink suggestions, M/M, Masochism, Oral Sex, Panty Kink, Pet Play, Rope Bondage, Spanking, Sub Dean, Temperature Play, Top Castiel, Top Dean, Whipping, lots of kinks
Language: English
Status: Completed
Published: 2015-07-08
Updated: 2016-03-23
Packaged: 2018-04-08 06:05:04
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 19
Words: 27,422
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4293570
Author URL: https://archiveofourown.org/users/KasMarie/pseuds/ArtemisAnne
Summary: <blockquote class="userstuff">
              <p>Dean and Castiel's Dom/sub relationship grows. Dean has trouble coming to terms with new desires. Cas opens up about his journey through kink. Jimmy has a few secrets of his own. </p><p>If you haven't read the first fic in this verse it's not required...but encouraged because it establishes their relationship and this will make more sense if you read that first. </p><p>If you're already a fan...welcome back. I couldn't stay away.</p>
            </blockquote>





	1. I Can Take It Baby, It's All Right

Dean knelt in the center of the bed with his wrists crossed behind his back. The blindfold he'd been instructed to put on obscured his vision and kept him surrounded in darkness. He shivered as cool air drifted across his bare skin. 

“Beautiful,” Cas growled out. 

Dean warmed under the praise. He felt a flush steal across his chest. No matter how many times his fiance had seen him in nothing but panties Dean still blushed. 

Cas trailed fingertips down Dean's spine. “Sam is staying with Jo tonight, why don't I warm up that ass of yours?” 

Dean pressed his lips together and nodded. He hadn't been given permission to make noise yet. 

“Good,” Cas whispered as he pushed Dean over on all fours. 

Dean arched his back and canted his hips, silently begging for what he wanted. 

Cas obliged. His hand reared back before cracking over the lace covered skin of Dean's ass over and over. 

After a handful of spanks Cas said, “You may make noise.” He loved Dean's obedience but couldn't stand having those pretty sounds hidden for long.

Dean moaned and leaned his upper body into the mattress. Heat spread across his ass and went straight to his hardening cock. 

He wanted more but he didn't know how to ask for it. He wasn't even sure what “more” meant but the word kept rebounding through his pleasure soaked thoughts. More more more.

“More what, gorgeous?” Cas whispered. His hand paused to rub along the hot skin.

Dean whined and rocked back into Castiel's touch. He shook his head and gripped the the sheets hard enough to turn his knuckles white. 

Cas frowned. Normally he could read Dean perfectly but he was at a loss. He couldn't figure out what Dean wanted if Dean wasn't even sure. 

“Shh shh, it's okay,” he cooed as he ran a hand up and down Dean's spine. 

Dean's body began to shake and he felt tears leak out behind the blindfold. His safeword was on the tip of his tongue when Cas whispered out, “Red.” 

The breath exploded out of Dean in a hard rush and he collapsed onto the bed. “I'm sorry. I'm sorry.”

Cas leaped onto the bed and pulled Dean close. “You have nothing to be sorry for, Dean. The scene broke. It happens. It's no one's fault.” 

The men lay together for several minutes, soaking up comfort in each other. Cas pulled the blindfold off but left Dean in his cuffs, sensing the sub needed the extra sensation to keep him grounded. 

“Do you want to talk about it?” Cas asked as he swept a hand through Dean's hair. 

Dean frowned. “I don't know.” 

Castiel's hand stilled. “You don't know if you want to talk or . . .?” 

“I don't know what happened.” 

Cas started petting Dean's hair again, fingernails scratching lightly with each pass. “Tell me what had your mind working so hard.” 

“More.” 

Cas hummed a thoughtful note. “More. Okay. You don't know more what, I'm guessing.” 

Dean made a frustrated sound and buried his face in Castiel's chest. 

“Dean?” Cas whispered. He waited until those gorgeous green eyes fixed on his. “Do you think you want more pain?” 

Dean jerked back and frowned hard. “What?” 

Cas raked his eyes over Dean's stricken expression. “Do you remember when I asked if you wanted more intense impact play?”

Dean nodded, his eyes narrowing. They'd been dry humping on the couch. 

“Do I have your permission to try?” Cas asked. “Not right now, obviously. Neither of us is in a proper state of mind for a scene, but I think next time. . .” 

Dean's stomach churned but not with anxiety. No, that was excitement swirling in his gut. 

“I'm not a freak, Cas.” 

He should have known better. Dean found himself pinned to the mattress with Castiel looming over him.

Cas gripped Dean's chin. “I've told you I don't appreciate negativity directed at my submissive. What have I told you about exploring your kinks?”

“What kind of person gets off on pain? A spanking here and there is fine but more than that. . .” Dean clamped his mouth shut and turned his head. 

Castiel sat back on his ankles, settling his weight across Dean's thighs. His hands went to his hips for a second before he reached for his phone and began tapping out a text message. 

Dean looked at his partner incredulously. He was texting at a time like this? Rude. 

Cas nodded at his phone before leaning down to kiss Dean chastely on the lips. “Get dressed. Jimmy is coming over.” 

Dean blinked rapidly. “I'm not following.” 

Cas pulled back and tilted his head to one side. “Jimmy didn't tell you?” 

“Apparently not.” 

A slow smirk crept across Castiel's face. “That asshole. I assume he would have mentioned it when he took you for pie that night.” 

Dean leaned up on his elbows. “Still lost here, babe.” 

“Jimmy's a submissive masochist, Dean. He's actually the one that introduced me to the lifestyle.” 

Dean raised an eyebrow. 

Cas slapped a hand down on his bicep. “Not like that, you pervert.”

Dean laughed and shoved Cas over so he could roll off the bed and find his pants. “I don't know this story.” 

“Another time. My journey. . . is complicated.” 

The front door opened and closed as Dean hurriedly finished pulling jeans over his panty-clad ass. “Why did we give that asshole a key?” 

“That was poor planning on your part,” Jimmy agreed as he sauntered into the room. “Because I have no sense of boundaries.” 

Dean shook his head and finished buttoning his jeans. “Quit looking. Cas will dig your eyeballs out with a spoon.” 

“Nah,” Jimmy shrugged. “Cas is all classy and shit. I'm sure he'd use a melon baller or something fancy.” 

“Dean is correct. Please stop looking at my fiance's cock.” Cas said drily. 

Jimmy shot Cas a wink. “But you buy such pretty things to put on it.” 

In a flash, Cas had Jimmy crowded against a wall with his hand on his twin's throat. “Mine, not yours.” 

Dean moved to interfere but watched as Jimmy relaxed in Castiel's hold. The normally brash twin lowered his eyes and let his arms fall to the side. Dean watched as Cas held the position for a beat before backing off. 

Jimmy blinked a few times before turning to face Dean, cocky expression back in place. He grinned. “We shocked your Adonis, brother.” 

“I assumed you would have told him during your heart-to-heart.” 

Jimmy crossed his arms over his chest. “With Moose sitting right there? I'm not active in the lifestyle anymore so that information is generally not public knowledge.” 

Cas scrubbed a hand over his face. “I forgot Sam was there with you. Apologies.” 

Dean cleared his throat. “So, it's true?”

Jimmy smirked. “Yep.” 

“No offense, dude. But you don't. . .”

Jimmy put a hand up. “Like everything about you screams sub?” 

Dean pursed his lips before nodding. “Fair enough.” 

Jimmy held out a hand, wiggling his fingers until Dean took it. “Come here, handsome.” 

Cas pressed a kiss to Dean's temple. “I'm going to get juice.” 

“But we didn't. . .” Dean trailed off at the look of authority on Castiel's face. 

Jimmy chuckled and tugged Dean's hand. “He's not in the mood to argue this afternoon.” 

The two men tumbled into the new king sized bed Cas and Dean had picked out when they officially began rooming together. Jimmy stretched out, pulling Dean's head to his chest. 

Dean had learned very quickly that the Novaks were a touchy feely bunch. He'd only just recently stopped tensing up every time Jimmy touched him. He'd been afraid of tripping Castiel's jealousy meter but his fiance only rolled his eyes at his twin's disregard for Dean's personal space. 

The truth was, Dean loved it. Not in a sexual kind of way, but in a “this is how comfortable we are around each other” kind of way. He actually thought it was awesome that he could relax and be himself around Jimmy and Anna without either thinking he was hitting on them. 

Cas returned with three glasses of juice gripped in his hands. He set them down on the side table before passing Dean and Jimmy each one. 

Dean shot Jimmy a playful glare. “How come you get my juice?” 

Jimmy's answer was a loud gulp followed by an extended _ahh_ sound. 

Castiel rolled his eyes. “Children.”

“You love me,” Dean teased. 

Cas huffed and leaned in for a kiss. “Very true.” 

Jimmy faked a gag. “I came to talk about kinky sex not watch you two be all gross.” 

Dean handed his empty glass to Cas and leaned back on Jimmy's lap. “So talk.” 

Castiel laced his fingers with Dean's as he laid in the small space next to him on the mattress.

“I assume my baby brother had the 'it's okay to be a kinky sex fiend' talk with you already?” Jimmy teased as he ran his fingers through Dean's hair. 

“He asks because he gave me the same talk when I was starting out,” Castiel interjected. 

“I can feel you rolling your eyes, Jimmy.” Dean teased. 

Jimmy huffed and tugged at Dean's hair in retaliation. “Have you ever seen more intense play, Adonis? Outside of porn?” 

Dean frowned. “Like gone to one of those leather clubs or something? Hell no.” 

Jimmy hummed, sounding so much like Cas. “I have a friend from when I was still doing scenes. He's local. Amazing dominant sadist. I'd be willing to scene with him if you're more of a show than tell kind of guy.” 

Dean tilted his head to look at Cas. “And we would be. . .” 

“Watching and not participating,” Castiel finished. 

Dean sat up suddenly. “You told me once you weren't into the S and M parts of the acronym.” 

Jimmy's whole body tensed and he held his breath. Dean gave him a wide eyed glance, afraid he'd fucked up. 

Cas ran a hand through his hair and blew out a breath. “That's due to the part of my journey we haven't discussed. You're different, Dean. You tried new things for me. Trust me when I say I'm okay and I want to do this with you.” 

Dean melted. “I'm not even totally sure I want this, Cas. I don't know what I want.” 

“We can find out together,” Castiel whispered as he leaned in to take Dean's lips. 

Jimmy growled playfully and shoved out from under Dean. “I'm gonna make a call before I vomit.” 

Dean licked into Castiel's mouth and shot Jimmy the finger over his shoulder. He always was good at mutli-tasking.


	2. I Take You Places You've Never Been

**Summary for the Chapter:**

> Dean scrambled off the bed. It was _his_ apartment after all. He should have some idea in the kind of people being given his address. 
> 
> He stopped short when he realized who was standing in his doorway holding a duffle bag and wearing a shit-eating-grin. 
> 
> “Benny?!” Dean exploded.

**Notes for the Chapter:**

> NOTE! If you're seeing this as labeled Part 5 you aren't imagining it or missing anything. I have NO idea why it's doing that :/ Sometimes I click and it's Part 5 and others it's Part 2. No idea.

Jimmy walked back into the room as he shoved his phone back in his pocket. “He'll be here in 30.” 

“Minutes?” Dean squeaked. He coughed and cleared his throat. “We're doing this tonight?” 

Jimmy looked hesitant. “Is that not okay? I can call him back.” 

Castiel sighed and placed a finger over Dean's lips, earning a glare. “That's fine, Jimmy. Dean will talk himself out of it if we wait.” 

Dean nipped Castiel's finger lightly before puffing out his lower lip in a pout. “Dick.” 

Cas shook his head and unfolded himself from the bed. Dean could all but see the Dom roll through him as he approached Jimmy. “What do you need?” 

Jimmy blew out a short breath and ran a hand over his face. “Water for sure. Juice is good but I prefer a sports drink if you have it.” He raised his eyes to meet Castiel's. “I'm a fan of chocolate after too.” 

Cas tilted his head back in thought. “I can offer you most of those. I believe we're out of chocolate.” 

“Chips!” Dean interrupted. He had to swallow hard and tilt his hips to avoid showing the erection he started sporting when those twin sets of blue eyes locked on him. “We have chocolate chips. I bought some to make cookies.” 

Jimmy's eyes danced with mirth as he flicked his gaze toward Dean's crotch briefly before winking. “That's acceptable.” 

“Do not encourage him,” Cas said to Jimmy as he bit back a grin. 

Jimmy only licked his lips. “He knows it'll never happen, dear brother. But he's fun to tease.” 

To Dean's absolute horror Cas began nodding. “You have a point. I'll have to keep that in mind. I'm sure he'll earn a punishment at some point.” 

Dean would deny the whimper that left his lips until he died. Shit. Like Castiel's sex voice doing regular dirty talk wasn't enough? The next time Dean wasn't allowed to come he'd have to listen to twin fantasies? Fuck. 

Dean cleared his throat again. “So, what, uh, what's the plan?”

Jimmy leaned on the doorframe and checked his phone for the time. “This guy knows all my buttons. My hope is that you'll see it's okay to like some of the more intense stuff. And maybe seeing it in person, with someone you trust to not lie to you, will make you more comfortable. Who knows? Maybe you'll walk away with an idea or two.” 

Dean frowned. “And you're cool with this? Just inviting some guy over and letting him hurt you?” 

Jimmy shook his head. “He's not just some guy off the street. We scened regularly when I was still doing it.” 

“I thought you didn't fuck the same guy twice,” Dean said. 

Jimmy opened his mouth to answer when a knock sounded at the door. He shut his mouth and went to answer it. 

Dean scrambled off the bed. It was _his_ apartment after all. He should have some idea in the kind of people being given his address. 

He stopped short when he realized who was standing in his doorway holding a duffle bag and wearing a shit-eating-grin. 

“Benny?!” Dean exploded. 

“Wait, you two know each other?” Jimmy said in between giggles. 

“We work together,” Benny confirmed. 

Castiel leaned against the wall and smirked. “You didn't say anything.” 

Benny rolled his eyes and dropped the bag on the floor. “Because 'hey, your boyfriend looks like this guy I used to whip and fuck sometimes' is a real great icebreaker.” 

“I didn't know you were into this kind of stuff,” Dean mumbled. 

“It's not exactly a work topic, cher. I had my suspicions when you came in sportin' that nice collar of yours but it wasn't my place to say anything.” 

Jimmy turned his baby blues on Dean. “You're still okay with this? I would have asked if I'd known.” 

Dean shook himself and smiled. “I'm surprised but it's cool. It's actually better. I trust Benny too so it's not some random dude in here.” 

Benny turned to Jimmy. “Boxers. Move the table and wait for me in the living room.” 

Dean watched as Jimmy ducked his head in acknowledgment before hurrying off. 

“Normally I gag his smart mouth but it's been awhile so I want him to be able to safeword easier.” Benny shifted his eyes toward Dean. “And I don't like to freak out newbies.” 

Dean couldn't find it in himself to be offended at the accusation. He was a newbie comparatively speaking and he was a little freaked out. 

Cas took Dean's face in his hands. “Your safeword works here tonight as well. If you're uncomfortable do not hesitate to let me know.” At Dean's nod he placed a kiss on his forehead. “Go wait for me on the couch. I want to chat with Benny.” 

Dean stumbled into the living room, glad to be instructed to sit before he fell. He made eye contact with a grinning Jimmy as his ass hit cushion. Jimmy shot him a wink as he raised up on his knees and placed folded hands behind his head. He almost looked like he was getting arrested but Dean could see how the position showed off his body. 

He made a mental note to try it next time he was alone with Cas. 

Benny and Cas entered the room and Dean made a split second decision to toss a pillow on the floor before kneeling. Cas settled onto the couch and ran a hand through Dean's hair with a pleased sound that wrapped around Dean like a blanket. Out of the corner of his eye, he caught the look of approval that Benny shot Cas. 

Jimmy trained his eyes to the floor but didn't stop the grin that spread across his face. 

“Been a long time, Jimmy,” Benny's deep voice rumbled out. 

“Yes, sir.” 

“Do you remember your safewords?” 

Jimmy nodded. “Red to stop. Yellow to slow down. Green is good.” 

“Arms down.” Benny reached into his bag and brought out a flogger. He trailed the leather pieces over Jimmy's shoulder, smiling when Jimmy hummed and leaned to expose more skin. 

“Did you miss me, cher?” Benny asked as he continued to pet Jimmy with the flogger. 

“Yes,” Jimmy whispered, his eyes closed. 

“Stand up.” 

Jimmy obeyed, huffing lightly as he pushed to his feet. Benny let him have a moment to shake out his legs and regain blood flow. At Jimmy's nod, he began to flick over his skin with the flogger. 

Dean watched, entranced. He had no idea how Benny could be so precise with something that covered so much area with each blow, but he could tell the man was avoiding sensitive areas like Jimmy's spine and kidneys. 

After several passes, the sound of leather hitting skin intensified. Dean could hear the pattering pick up as Benny used more force. 

Jimmy was swaying in place. He made little punched out sounds of pleasure each time the flogger connected with his skin. 

“Warm?” Benny asked. 

“Green,” came Jimmy's reply. 

“We don't have my bench here so you'll have to bend over the arm of the couch.” 

Jimmy nodded in a dazed way as he moved into position. Dean could see his eyes were already a bit glassy with pleasure and he looked utterly relaxed. He folded himself along the arm of the couch, arms outstretched enough to grip the edge of the cushion. His head tilted to one side and Dean could see his eyes blinking in a slow pattern. 

Benny stepped behind him and placed one hand at his lower back. “Can I go ahead and remove these?” 

“Green,” Jimmy replied. 

Dean tilted his head to look at Cas with an eyebrow raise. Cas only shook his head and tapped a finger to his own lips to indicate they were to stay quiet. 

The sound of skin slapping skin brought Dean's attention back. Jimmy groaned long and low as he melted further into the couch. The sound of each spank Benny laid out was loud and Dean could tell he was hitting with quite a bit of force. 

Each spank was followed by a gasp and groan from Jimmy. His body would tighten with each blow before relaxing again. 

When the whimpers began, Dean realized he was hard. Motherfucker. He was getting off on watching his friend beat on his fiance's twin brother. 

Next up, on Maury. 

Benny ran a hand up and down Jimmy's spine a few times like he was soothing a skittish horse. 

“Please,” Jimmy rasped out. 

Dean's brow furrowed in confusion. Please what? No one had asked anything. 

But when Benny moved to the bag Dean realized no one had to. Jimmy said he and Benny had scened together several times. Dean bet Benny could read Jimmy like Cas read Dean. 

Benny returned with a coiled length of supple leather in his hands. Oh, a belt. He was folding a worn leather belt in half. 

“Ten,” Benny said as he dragged the belt down Jimmy's spine. “Count.” 

The sharp _crack_ that split the air made Dean jump. The harsh gasp it pulled from Jimmy made Dean want to jump up and rip the belt from Benny's hands. . . 

Until the man across the couch moaned. “One.” 

The air stilled in Dean's lungs. Holy fuck. Jimmy liked it. He fucking liked it. There was no way he was faking that pleased as punch moan. 

Dean didn't realize he'd stopped breathing until Castiel's hand came down on the back of his neck. He sucked in a fast breath and let it out audibly enough that Cas relaxed. 

They were up to six and Jimmy was all out humping the edge of the couch. Dean had a fleeting thought of wishing they'd put down a towel. 

Seven and eight cracked down in rapid succession and Jimmy said the numbers on a sobbing moan. 

The moan after nine had Dean's hand flashing down to grip his cock to relieve some of the pressure. What were the odds that Cas would let him run to the bathroom and jerk off? The brief hint of pressure at the back of his neck said his Dom knew what he was thinking. 

He was so caught up in his horny thoughts he almost missed the final crack of belt across skin. He couldn't, however, ignore the shout of “TEN!” followed by harsh breathing that came from knowing you weren't going to get to come that night. Dean knew that pattern quite well. 

“Dean,” Cas said quietly. “Please go to our room and get the aloe gel for Benny.” 

Dean didn't hesitate to comply. He leaped up, as much as he could with his raging hard-on, and raced to their room. 

The gel stayed in the side table with the lube and toys for easy access so it was a quick grab. He made his way back to Benny and stopped dead in his tracks. 

Jimmy's poor ass. 

Wordlessly, Dean handed over the gel as he stepped closer. Benny moved enough for Dean to survey his work while still staying close enough to tend to Jimmy. 

Jimmy's entire backside was a brilliant red. Dean could see the crisscrossing welts from the belt along with a few finger outlines along the edges. Dean leaned in the best he could but he couldn't find any bruising or bleeding. Damn. Benny was good. 

Jimmy whimpered and writhed as Benny applied the gel with gentle motions and whispered praise. Dean went to the kitchen to help Cas get recovery snacks. He felt like he was intruding on something. 

Cas greeted him with a gentle kiss. “Doing okay?” 

“Is Jimmy gonna be okay?” Dean whispered. 

Cas smiled. “He'll be sore and he might have some light bruises but he's fine.” He handed Dean a bottle of sports drink before rooting around in the pantry for the chocolate chips. He poured a few into a small bowl and gestured for Dean to lead the way back to the living room.

Benny was seated on the couch with Jimmy curled in his lap covered by a blanket. His hand ran rhythmic circles on the dark haired man's back. Occasionally Jimmy would make a small contented noise and nuzzle into Benny's neck. 

Dean handed him the sports drink while Cas put the bowl of chocolate on a side table. Benny accepted both with a head nod and grin. 

Jimmy started to rouse a bit with the new presences. Benny helped him sip the drink before hand feeding him individual chocolate chips until he was more aware. The two shared a few sweet kisses that made Dean blush. 

Jimmy blinked slowly at Dean. “You okay over there, Adonis?” 

“I think I should be asking you that,” Dean replied. 

Jimmy stretched and sighed. “I'm awesome.” 

Benny dropped a kiss to his neck. “Do you have someone to drive you home?” 

“He's staying here tonight,” Castiel interrupted. 

Jimmy shook is head with a smile. “You heard the Dom.” 

“You know the drill,” Benny said. 

“Call in the morning and text throughout the day.” Jimmy stood slowly, keeping the blanket wrapped around himself. 

Benny cupped his face in a large hand. “It's been a while. I don't want you to drop too hard, cher.” 

“Thank you,” Jimmy whispered as he leaned in for a kiss. 

Cas walked Benny out while Dean helped Jimmy get set up in their extra room. He worked in silence, unsure of what to say or how to organize his thoughts. 

One thing kept replaying in his mind, however. 

He wanted to try.


	3. I slipped and then I fell

**Summary for the Chapter:**

> Sam turned to Dean. “Which one of you?”
> 
> “Benny,” Dean replied. 
> 
> “But why would Benny. . .”
> 
> “Because I asked him to,” Jimmy said around his next mouthful. 
> 
> Sam blinked hard a few times. “I don't feel drunk enough for this conversation.”

**Notes for the Chapter:**

> This goes someplace kind of dark. No graphic descriptions but there is a story of violence (per usual with these things right?) I'll TL;DR in the end notes for those that are uncomfortable or need a spoiler warning before reading.

The next morning Dean sat at the kitchen table eating cereal while Cas showered. Jimmy shuffled in, thankfully wearing a borrowed set of pajamas. He was pouring his own bowl of breakfast when Sam came home. 

“Dean, why is your fiance wearing my pajamas?” Sam asked. 

Dean saw a mischievous smile cross Jimmy's face and pointed his finger. “Don't.” 

Jimmy pouted and turned to put the milk back in the fridge. 

Dean shook his head. “Cas is in the shower. Jimmy stayed the night.” 

Jimmy hissed as his ass hit the chair. He shifted a few times before he got comfortable.

Sam raised an eyebrow. “Everything okay over there?” 

“Got my ass beat last night.” Jimmy answered as he spooned up some Lucky Charms. 

Sam turned to Dean. “Which one of you?”

“Benny,” Dean replied. 

“But why would Benny. . .”

“Because I asked him to,” Jimmy said around his next mouthful. 

Sam blinked hard a few times. “I don't feel drunk enough for this conversation.” 

“You didn't have to _watch_ ,” Dean stated tartly. 

Jimmy snorted. “He probably wouldn't have gotten hard if he had.” 

“Oh fuck me,” Dean groaned. 

“I've told you I don't share,” Cas said as he entered the conversation. 

“Plus he's your brother,” Jimmy mused. 

Sam's eyes pinged around the room. “Is it always like this?” 

“Yep,” the trio answered in unison.

Sam made his way to the coffee maker and began pouring a cup. “So what's this about Benny?” 

“Apparently he's a sadist,” Dean said with a thoughtful frown. 

“Um, disturbing.” Sam's brow furrowed as he stirred in his creamer. 

Jimmy shrugged. “They removed sadism from the DSM a few years ago. It's perfectly acceptable when you throw some consent in there.” 

“And he had it?” Sam asked. 

Jimmy rolled his eyes. “Duh.” 

“Yeah, dude. You think I'd let someone beat on Jimmy without his okay? You think Cas would allow it?” Dean asked. “Besides, you dated a masochist. No judging.” 

Sam took a sip of his coffee. “True. It's just weird because 'sadist' is usually used when discussion serial killers or something.” 

“Society sucks,” Jimmy pouted into his bowl. 

Sam snagged a banana from the counter. He peeled it while he said, “So why was there a show I, thankfully, missed?” 

Dean frowned again. “I might be a masochist.” 

“Huh,” Sam said as he took a bite. 

Jimmy pinned Sam with an overly lascivious leer. Dean was confused until he realized Jimmy was watching Sam eat the banana. 

Dean kicked him under the table. “Dude, gross.” 

“He started it.” Jimmy threw Sam a wink. 

Sam flushed. “Oh my God.” 

“Ooh baby, talk dirty to me.” Jimmy let out a fake moan before he began cackling. 

Even Castiel cracked a smile. 

* * *

Dean flopped face down on the bed and burrowed his face into a pillow. He felt Castiel slide in next to him and begin pressing kisses to his neck. 

“Are we gonna talk about this?” Dean rumbled. 

“You want to talk about it?” Cas asked, his tone surprised. 

Dean shrugged and rolled so he could face his fiance. “You're okay that I basically got off to watching your brother get off?” 

Castiel rolled his eyes. “Dean, I don't get upset when you watch porn. We just happened to have live porn and know the actors. I was there with you and you didn't cheat on me. Sharing DNA is the only reason I didn't have a similar reaction.” His smile turned wicked. “Although, later when I imagined you in the same position. . .” 

Dean swallowed hard. “Yeah?” 

“Mmhmm,” Cas hummed as he leaned to bite down on the chords of Dean's neck. “All spread out and whimpering for me? Begging? You know that's my favorite.” 

Dean shivered. “Really? I thought your favorite was my cock down your throat.” 

Castiel rutted his hard cock against Dean's hip a few times before stilling himself with a deep breath. “As much as I'd love to fuck you senseless, we do need to talk about last night.” 

Dean groaned and rolled back so his face was in the pillow again. “Caaaaas.” 

“Dean.” Castiel's voice was soft but whip sharp. “It is important that we communicate.” 

Dean huffed a sigh before rolling back to face his Dom. “I liked it.” 

“Would you like to try it for yourself?” Cas raked his eyes across Dean's face, watching his expression carefully. 

Dean swallowed hard and closed his eyes. “Yeah,” he said in a small voice.

“Next question. Would you feel okay having Benny and Jimmy in attendance for guidance?” 

Dean's eyes flew open. “But you don't share!” 

“I would only be sharing the experience, not your body or your submission.” Cas shifted a bit. “I'm not comfortable going at it alone for your first time.” 

Dean sat up, a worried expression in place. “What aren't you telling me, babe?” 

Cas turned his back to Dean and put his head in his hands. He sat silently for several breaths. When he spoke, there were tears in his voice. 

“I hurt someone, Dean.” 

Dean felt the air ripped from his lungs. The pain surrounding Cas was palpable and Dean didn't hesitate to wrap his arms around Castiel in a tight embrace. 

“We don't have to talk about it if you don't want to,” he whispered. 

Cas shook his head. “You need to know before we get into it. Communication, remember.” 

Dean settled back against the headboard, pulling Castiel into his arms as he went. 

Cas settled against Dean's chest with a pained sigh. “I went with Jimmy to a club one night after he explained it all to me. We were young, barely of age to be in such a place but Jimmy worked with the guy that ran front security. 

“He was enamored with the lifestyle and wanted me to at least check it out. He said he felt like I'd enjoy the domination side of it and he always could read me pretty well. So I went. I told him from the start that I was just going to watch. He promised he wouldn't leave my side for a second and vowed not to play that night either. 

“We watched a few scenes in the public play area. I could see what he meant and immediately put myself in the shoes of each Dom we watched. It was . . . exhilarating. I felt like someone reached in and found a piece of myself I hadn't known was missing and showed it to me. 

“I ended up going back, alone, the following weekend. It was like a drug. I couldn't get enough of the sexually charged atmosphere and I wanted to learn more. I needed to see more. So I paid for a special membership that let me in to the private rooms. Some of the rooms were set up with a viewing area for those into exhibitionism. These couples tended to be more established and intense. 

“That's where I met Naomi. She was a well-known Domme in the club and had a male submissive named Alfie. He wasn't my usual type but the innocence and naivety in his eyes hadn't been stripped from him yet. I returned several times to watch their scenes in particular. Naomi noticed and approached me one evening asking why I didn't bring my sub to play. When I explained I was new and unattached she offered to take me under her wing and show me everything she knew. She invited me to her private home so I could learn without the distraction of an audience.

“I hadn't done my research. I didn't know what made a good or bad dominant. I relied on what Naomi told me instead of my own feelings. Any time I felt uncomfortable with what she did I chalked it up to lack of experience on my part and pressed on.”

Dean's arms tightened as the tears returned to Castiel's voice. He pressed a kiss to his lover's hair and soothed his hands up and down Castiel's arms. 

Cas took a deep breath and let it out on a shaky exhale. His voice was thick when he continued. “It turns out Naomi was the bad kind of dominant. She enjoyed hurting and abusing her subs whether they liked it or not. She had them convinced that a safeword meant disappointment and her pleasure came first. Totally the opposite of everything I've come to believe in. 

“The last night I was with her, she had me whipping Alfie with a leather strap. He screamed and cried and begged me to stop. He was bleeding and nearly unconscious by the time he said a safeword. It turns out Naomi hadn't approved use of a safeword that night and told me to continue.” 

“Can she do that?” Dean exploded. 

“She shouldn't have but she did. I refused. She told me I'd never make it as a Dom if I let weak submissives walk all over me and make decisions for me. It didn't feel right. Everything I'd felt in the previous months came out at once and I realized I didn't want to be the kind of Domme Naomi was. So I untied Alfie and we left. I drove him to the nearest emergency room and stayed with him while he got treatment.” 

“Was he okay?” Dean whispered. 

“Most of the wounds were superficial and he was exhausted. They kept him overnight and pumped him full of fluids before releasing him. I made sure she was blacklisted from the club and circulated her name in as many circles as possible as a warning. Apparently, she'd been banned from several other clubs for similar behavior. Alfie wasn't her first victim.” 

“Did you report her to the police?” Dean asked. 

“I tried, but one of the guys at the club was on the force. He said it was difficult to get anything done because Alfie had consented to be there and most people don't understand how the dynamic works. There's so much prejudice against this lifestyle. As far as most of his coworkers were concerned, Alfie 'got what was coming to him' and should have known better.” 

Dean felt sick. “That's disgusting. No one deserves to be treated like that.” 

“We know that, but too many people don't.” Cas sighed and scrubbed a hand down his face. “She's gone anyway. She just cleared out one weekend. No one has heard from her since.” 

Castiel sat up and faced Dean. “So that's my story. After Naomi, I refused to participate in anything heavier than what we've done. In the past, I've turned down scenes because the submissive wanted something more intense. Jimmy tried several times to get me to see it done properly but. . .” 

Dean put his fingers over Castiel's lips. “We don't have to if it's going to trigger something bad for you.” 

Cas shook his head. “The other night with Benny and Jimmy helped me as much as it did you. Seeing them together; doing something intense with success and care was beautiful. But that's why I want them there to help me.”

“I trust you, Cas.” 

Castiel's lips turned up in a sad smile. “You shouldn't.” 

“No,” Dean barked. “You don't let that bitch decide anything for you. I trust you with everything, Cas. I wouldn't wear your collar if I didn't. If you need Jimmy and Benny there to feel comfortable then that's what we'll do. But don't do it just for me and don't let Naomi's memory taint what we have.” 

Castiel closed his eyes and tears tracked down his cheeks. Dean reached up with his thumbs and brushed them away, cupping Castiel's face as he leaned in for a soft kiss. 

“I love you,” Dean whispered. 

“I love you, too.” Cas pressed his fingertips to Dean's lips before placing them on his own. “I want to try. I think I need to try.” 

“Then that's what we'll do. I'll talk to Benny at the garage tomorrow.” 

Cas nodded. “I'll talk to Jimmy. We'll work something out.” 

Dean pulled Cas against his chest once more, spooning in behind him as the emotions took their toll. He hadn't been lying. He trusted his Dom with everything and wanted to experience this with him. 

He just had to help Castiel remember how to trust himself again.

**Notes for the Chapter:**

> TL;DR  
> Cas was trained by Naomi before he knew better and ended up hurting Alfie at her command.


	4. Make Me Shiver When You Touch My Skin

**Notes for the Chapter:**

> Sorry for the delay. I won't bore you with life details but things are hectic right now! I haven't forgotten you or abandoned this fic...just fewer Muse visits these days. 
> 
> Comments feed my soul!

Dean slid into the booth opposite Benny with a sigh. “Thanks for coming out with me, man.” 

Benny nodded as the waitress left with their drink orders. “Can't say I'm surprised. What's on your mind?” 

Dean fiddled with the napkin for a bit before raising his eyes to meet Benny's. “Cas wants you and Jimmy to help us with a scene.” 

“Okay,” Benny said as he leaned back. “Is that all?” 

“Yep.” 

Benny raised his eyebrows. “You sure?” 

Dean's eyes narrowed. “Are you pulling some Dom shit on me?” 

“Do I need to?” 

Dean sighed and scrubbed a hand at the back of his neck. “Cas hurt someone. He had a bad teacher and it put him off intense play. He's scared.” 

“Are you?” Benny took a sip of the soda the waitress dropped off. 

The men placed their orders and sat in silence for a minute after the woman left. 

“No,” Dean whispered. “He thinks I should be, but I'm not. I trust him. What happened really wasn't his fault. He knows better now.” 

Dean relayed the story to Benny, feeling a bit squeamish when the normally happy man's eyes darkened to something akin to rage. 

“It's a good thing that bitch is gone,” Benny growled. “People like that are what give people like me a bad reputation.” 

Dean was nodding. “Seeing how you were with Jimmy . . . I think it gave Cas hope. He wants to try, for me.” 

“Can I ask a few things?” 

Dean lifted his palms in an open gesture to indicate Benny should go right ahead. 

Benny watched Dean for a beat before sighing. “The best way to teach is to show and participate. Did you guys think about that?” 

Dean blinked slowly. “I don't understand.” 

“I can't teach Castiel what you like if I don't know, Dean.” 

Realization dawned slowly. “So you'd be. . . with me?”

Benny nodded. “Possibly. It would be best, actually.” He held his hands up in a supplicating gesture. “Nothing sexual. I have no inappropriate feelings for you, brotha.” 

Dean shot him a crooked grin. “Cas would castrate you.” 

“I figured. But you need to make sure he's okay watching me have that kind of position over you, even just once. It would be best if he would practice a little with Jimmy too but I don't know how he'd feel about that bein' twins and all.” 

Dean munched on a fry from his plate. “Jimmy would be down, that kinky motherfucker.”

Benny threw his head back with laughter. “You don't even know.” 

Dean groaned. 

* * *

Dean found his fiance in their kitchen, ass swaying to the radio as he stirred something on the stove. 

Dean pressed behind Cas, his hands finding their way to slim hips. “Where's Sam?” 

Cas leaned his head back against Dean's shoulder, exposing the long line of his neck. “Jo's. Again.” 

Dean took advantage of the skin being presented and began pressing kisses there. “That boy needs to grow some balls and move in with her.” 

Castiel hummed as he began to grind against Dean's erection. “And what would we do with an empty apartment all to ourselves?” 

“Do you want the list? You'd never be allowed to wear clothes and I'd be able to routinely fuck you until you scream.” Dean punctuated his words with a firm bite to the chords of Castiel's neck. 

In a flash, Dean found himself pinned to the wall with Castiel's hand at his throat. 

“And what makes you think you make the rules?” Cas asked, his voice dipping into _oh shit_ territory. 

Dean whimpered as lust shot through him. 

Cas applied the slightest bit of pressure to Dean's neck. Not enough to cut off his air, but enough that he could feel it. “What if I want you in nothing but panties at all times? What if I demanded that you stay prepped for me so I can bend you over whenever I want?” 

Dean rode Castiel's thigh where it was lifted between his legs, chasing the friction with reckless abandon. 

“In fact, why don't you go do that. Prep and panties. I want a treat after dinner,” Castiel purred before grinding his leg against where Dean's erect cock was trapped in his pants. 

Dean whimpered when Cas pulled away. It took several deep breaths before he could make his way to their room. He stripped down and lay spread eagle on the bed for a few seconds. If he started fingering himself immediately he'd come without permission. 

Once he was calm enough, Dean slowly worked himself open for his plug. Cas hadn't specifically mentioned the plug but “prep” usually meant to use it. 

Plug situated, he pulled open his panty drawer. A smirk crossed his features as he thought back to the day he'd discovered he needed an entire drawer for his panty collection. He rarely wore anything else when it was just he and Cas. He was careful to wear briefs over the top if he wore some to work, in case his pants slipped at all. 

A pair of lemon yellow lace boy shorts were pulled up his legs. The bright color made his skin look even more tan. They had been a gift from Castiel as Dean wouldn't have picked the vibrant hue on his own but had come to love it. 

Dean made his way back to a kitchen filled with a pulsing beat. Cas had stripped his shirt and was swaying to the music, his jeans sliding lower on his hips with each undulation. 

Dean couldn't help himself, he pressed his body to Castiel's and brought them into a thrusting rhythm. Cas turned in his grip and slotted their hips together with a smooth roll. 

_You do it to me so well_  
_Hypnotic takin' over me_  
_Make me feel like someone else_  
_You've got me talkin' in my sleep_

Cas slipped his hands into the back of Dean's panties, gripping his ass firmly before scratching his nails. A hiss followed by a low groan erupted from Dean. 

_I don't wanna come back down  
I don't wanna touch the ground_

Dean whimpered when Cas wrapped a hand around his neck and licked across his lips. 

_Hypnotic takin' over me_

Cas ran light fingertips over Dean's leaking cock where it was visible at the waistband of the panties. He brought precome wet fingers to his lips and sucked, only breaking eye contact with Dean when his eyelids fluttered with pleasure. 

Their lips met again and Dean could taste the hint of himself in Castiel's mouth. 

Cas pulled back with a small grin. “Bend over the table.” 

“What?” Dean asked, his voice cracking on the word. 

“Table. Bend over. I won't ask again.” 

Dean rushed to obey. He spread his legs the way he knew Cas liked. 

Cas ran a hand up the outside of Dean's quivering thigh. “I love these gorgeous bowlegs of yours.” He leaned down until his chest pressed against Dean's back. “I love seeing them spread out underneath me.” He ground his hard cock against the plug in Dean's ass, pulling a series of high pitched whines. 

Cas kissed his way down Dean's spine, reveling in the way his submissive's breath caught with each press of lips to skin. When he reached the indents above Dean's tailbone he gave a long lick along the path he'd just blazed with his lips. 

He hooked the waist of Dean's panties and dragged them slowly down. “I thought I could wait until after dinner but you're far more appetizing at the moment.” 

“Life's short, eat dessert first?” Dean tried to joke. 

Castiel only hummed and bit lightly at the swell of his ass, causing Dean to yelp with surprise before moaning with pleasure. 

Cas teased the plug out with agonizing slowness and lots of twists that drove Dean to the brink of insanity. He tossed it on the floor, knowing they had plenty of cleanup ahead of them anyway. 

He pulled lube from his pocket and quickly slicked his cock. He filled Dean with one firm thrust. Both men cried out in unison as Cas began pounding in and out of Dean. 

“Touch yourself,” Cas barked out. 

Dean reached down to stroke his cock under the rough lace. “Oh fuck. Oh fuck. I'm gonna come, Cas.” 

Castiel's response was to bottom out inside Dean while leaning forward to bite his shoulder with enough force to bruise. 

Dean came with a shout, come surging onto the tabletop in front of him. 

Cas fucked into him faster. The punched out whines Dean was making combined with the hot vice around his dick shoved him over the edge with a low growl. 

Both men were breathing hard as Cas carefully slipped out of Dean. 

Dean straightened with a groan. “I'm getting too old for this 'not in the bed' shit, dude.”

“Did you not enjoy yourself?” Cas asked with an eyebrow raise. 

Dean wrapped his arms around Castiel and kissed him on the neck. “Of course I did. But now we have to sanitize everything or Sam will have a fit.” 

“How is Sam going to know unless you tell him?”

Dean smirked. “Little brother senses.” 

“That isn't a real thing, you ass.” 

Dean laughed as he grabbed supplies to clean the table. “You just wait.”

**Notes for the Chapter:**

> Song: "Hypnotic" by Zella Day (I love this song right now)


	5. I Don't Wanna Come Back Down

**Summary for the Chapter:**

> “Do you trust your sub to tell you when he reaches a limit?” Benny asked. 
> 
> “Of course I do,” Cas responded. 
> 
> “Start with five more,” Benny instructed.

**Notes for the Chapter:**

> I hope this turned out okay. I hope you like it. Thank you for sticking around! 
> 
> Warnings for heavier play in this chapter.

Dean sat at the table sipping orange juice. He and Cas were waiting for Jimmy so they could all ride over to Benny's together. 

He looked up at a key in the door but his hopeful expression changed when just Sam walked in. 

Sam stopped dead in his tracks in the kitchen. He looked at Dean, looked around, looked over his shoulder where Cas was walking up, and looked back at Dean. 

“Dammit, guys. The kitchen?” Sam whined. 

Cas glared at Dean. “You told him?”

“I did not!” Dean argued. 

Sam groaned. “But you just did.”

Cas put his hands on his hips. “How did you know? And don't give me shit about little brother senses.” 

Sam gestured to where Dean sat. “Dean looks smug as fuck.”

The trio looked over as the front door opened again and Jimmy joined them in the kitchen. 

The dark haired man looked around at everyone before cracking up laughing. “The kitchen!” he choked out in between breaths. 

Cas threw his hands up in exasperation. “Seriously?” 

Jimmy walked over and high-fived Dean. “Nice.”

“Don't encourage him,” Sam said, crossing his arms. 

Jimmy only laughed. “Too late.” 

Cas reached up to rub his temples. “I'm leaving. You're welcome to join me.” 

Dean and Jimmy jumped up and scampered after Cas. The three men settled into the Impala and headed to Benny's. Jimmy sat in the back to give the couple a little extra time together. 

Dean's stomach jumped when he pulled into Benny's driveway. He'd been there to have drinks after work before, but pulling up under these circumstances made the butterflies nesting in his stomach do the samba. 

He slipped lightly into sub-mode without a thought. He felt too overwhelmed to make his own decisions and immediately fell into step behind Cas. 

Jimmy let himself in and called out to Benny as the group made their way to the living room. The couch had a plate of cheese cubes and a plate of crackers sitting in the center and Dean saw two oversized pillows on the floor. Jimmy lowered himself to one and Dean quickly took the other. 

Cas sat on the couch and ran his hand through Dean's hair. “Gorgeous.” 

Benny entered and sat on the other side of the couch. “I thought we would sit for a bit before beginning. I figured you two would need a transition period.” 

Cas nodded. “That's very thoughtful of you.”

Benny shrugged and picked up a cube of cheese. He fed it to Jimmy before cupping the man's face and brushing a thumb against his mouth. 

Dean cleared his throat and looked to Cas, unsure of the protocol. 

Benny caught the gesture and grinned. “No need to be so formal, cher. I'm not one that cares if subs speak. Can you imagine Jimmy quiet all the time?” 

Dean chuckled. “I'm not sure that's possible.”

“It's not,” Jimmy added with a smile. 

Benny tugged lightly at Jimmy's hair. “It'd be boring as well. I don't mind his mouth as long as he's respectful.”

Dean snorted. “You and Cas seem to have that in common.” 

“However, a nice ball gag can produce fun sounds as well,” Benny said in a conversational tone to Castiel. 

Cas nodded thoughtfully. “I'll keep that in mind.” 

Dean's dick twitched and he blushed as he shifted on the pillow. Jimmy caught his eye and winked; which only served to make Dean blush harder. 

They sat for ten minutes making idle small talk and snacking on cheese and water. Benny and Castiel exchanged a glance that seemed to be a silent discussion in Dom Speak. They rose in unison and held out hands for Jimmy and Dean to follow. 

Dean had never been farther down the hall than the first door, guest bathroom, so he followed with caution. When they reached the end, he realized they'd bypassed Benny's bedroom in favor of . . .

Well, if he had to call it anything it would have been a dungeon. 

His grip on Castiel's hand tightened and Cas brought his opposite hand around to stroke Dean's forearm. 

Jimmy settled in to kneel on the floor with a contented sigh. 

Benny stroked the back of Jimmy's neck before turning to Cas. “Take your time.” 

Cas tugged on Dean's hand. “Let's look around. You'll feel more comfortable if you touch things and ask questions.” 

Dean nodded as he glanced around. His overwhelmed feelings must have shown on his face because Cas took charge and led him over to one wall. 

“This is a Saint Andrew's Cross,” he said as they stopped in front of a large X-Frame set against the brick. 

Dean reached out and ran his hands over the smooth wood and leather buckles. He shivered at the thought of being strapped standing in a spread eagle position, at Castiel's mercy. 

“Ready to move on?” Cas asked.

At Dean's nod he crossed to the other side of the room where Benny displayed various impact toys. Over the years, he'd accrued quite the collection. Paddles in various sizes hung next to leather straps and thin wooden canes. 

Dean tilted his head and touched a cane on the far end. 

“Small implements can hurt worse than something larger like a paddle. The swing and pain are more localized. Caning is not where you will be starting,” Cas explained. 

“Where will we be starting?” Dean asked. 

Cas gave him a soft smile. “Open hand and paddle. Nothing more than we've already done. Not at first.” 

Dean nodded. He could deal with that. 

“Feeling calmer?” Cas asked. 

“Yeah,” Dean said. “I'm good.” 

“Good.” Cas brushed their lips together before turning to Benny with a nod. “We're ready.”

Dean noticed Benny making his way toward the center of the room where a strange looking piece of equipment was located. 

It had two levels. Both padded and covered with black leather. Dean looked at Cas in confusion. 

“Spanking bench,” Cas said. 

Suddenly it made sense. Dean could see where his knees would go on the lower level while his upper body spread out across the top; putting his ass out on display. A whimper tore from his throat before he could stop it. 

Benny's booming laugh filled the room. “I guess he's okay with it.” 

Cas tapped the side of Dean's throat. “Safewords.” 

“Red to stop. Yellow to slow down,” Dean recited, the familiarity helping ease his nerves. 

“Strip as far as you're comfortable and get into position.” Confident his instructions would be followed, he made his way to the implement wall to pick out a paddle to use after he'd warmed Dean up with his hand. 

Dean focused on his task, stripping to his boxer briefs before folding his clothes. He didn't feel like going full naked in front of everyone and Cas had said as far as he was comfortable. He climbed up and knelt across the bench. 

Cool fingers danced down his spine and made him relax with a soft moan. 

“Normally one is bound to the bench but as it's our first time using it I'm going to leave your arms and legs free. I'd like you to remain in this position though. Lack of binding is not freedom of movement.” 

“Yes, sir,” Dean whispered. 

“Good boy,” Cas whispered back. 

Jimmy knelt in Dean's eye line. “Hey, stud.” 

Dean's response was a slow blink of acknowledgment. 

“Jimmy is going to sit there and help keep an eye on you,” Cas explained. 

“Mmkay,” Dean grunted, slipping more into his headspace even though they hadn't started yet. “Trust you, Cas.” 

Castiel's hand rested at the waistband of Dean's underwear. “Can I pull these down some? Just enough to bare your skin. I'd feel more comfortable if I could watch for damage directly.” 

Dean tensed but nodded. He jumped when Jimmy ran light fingertips down his nose. 

“Benny has his teacher face on, Adonis. No sexual feelings toward your ass that I can see.” 

The information helped Dean relax a little. It was still weird having his bare ass out in the open with his best friend from work watching, but he could deal.

Benny's deep voice reached Dean's ears. “Start like you usually do and go until you'd normally stop.”

Cas must have nodded because his hand immediately fell upon Dean's ass. The familiar sound and feeling of Castiel's spanks made Dean melt into the padded leather. He groaned softly as heat spread across his skin. 

When his entire backside was nice and warm, Cas rubbed gently. “I'm going to use the paddle now.” 

“Please,” Dean whimpered, lost in sensation. 

The sweet smack of leather on his inflamed skin had him keening with pleasure. Half a dozen blows fell in rapid succession and Dean grew harder than ever. Maybe he had a bit of an exhibition kink he didn't know about. 

Movement stopped and Dean whined as he canted his ass back as much as the position would allow. He didn't want to move too much and get in trouble but he wasn't ready to stop. 

“How's he doin'?” Benny asked. 

Dean felt a gentle fingertip caress his cheekbone. His eyes slowly opened to find Jimmy watching him with a small smile. 

“He's good,” Jimmy said. 

“This where you usually stop?” Benny asked. 

Cas nodded. “Yes. Normally we don't go deeper than this.”

“He's not ready to stop though, is he?” 

Cas swallowed hard, the sound clicking in the silent room. “No, but I–”

“Do you trust your sub to tell you when he reaches a limit?” Benny asked. 

“Of course I do,” Cas responded. 

“Start with five more,” Benny instructed. 

Cas trailed the paddle across Dean's ass. “Is that okay with you?” 

Dean could only whine again and press his hips back. 

“Words, Dean. I need to hear it.” 

“Yes,” Dean said. “Please, Cas. Don't stop.” 

“Jimmy, count for him,” Benny said. 

At Jimmy's nod, Dean's eyes slipped closed again. The first smack felt sharper than before even though he knew it was the same as the previous ones. The next came right on the heels of the first. He vaguely heard Jimmy whisper the numbers. 

He felt the endorphin laced euphoria wash over him. The buzz just under his skin fell silent. His thoughts quieted and he felt perfectly content. Somewhere in his mind he knew he was hard as a rock, leaking in his underwear as his friend looked on . . . but he couldn't bring himself to care. 

The last number fell past Jimmy's lips but Dean hadn't felt the spank land. 

“He's done,” Jimmy whispered. 

“Dean?” Cas asked, rubbing small circles over his lower back. “Can you hear me, gorgeous boy?” 

“Mmhmm.” 

Jimmy's pleased chuckle made Cas smile. 

“Do you want to come, Dean?” Cas asked. 

Dean shrugged. He felt so good it didn't matter. He'd probably care later but he'd worry about it then. 

Gel slick hands caressed his burning skin as Castiel rubbed soothing aloe across his ass. Dean hissed and jerked away but stilled when Cas made soothing noises. 

His underwear felt like sandpaper when it was pulled back up. Cas pulled lightly on his shoulder to get him to kneel up slowly. 

“Let's get him over to the bed,” Benny said softly. 

Bed? Bed sounded good. 

“Impressive,” Cas said. 

“Two queens pressed together. I made the frame myself,” Benny said with pride. 

Dean climbed into bed next to Cas and curled up against his warm body. When had Cas stripped down? They were skin on skin now; both in boxer briefs. 

Dean drifted for several minutes. He could hear people moving around him but the only thing that mattered was Castiel's heartbeat under his head. 

“Dean, sit up for me. There's juice,” Cas sang. 

Dean shoved upward with a groan. Goosebumps broke out on every bit of skin exposed to the air. He shivered as he sipped from the glass lifted to his mouth. Juice drained, he shimmied back under the blankets and snuggled close to Cas. 

He felt Castiel's hand rake through his hair and sighed. “I love you.” 

“I love you too. Are you coming back to me?” 

Dean stretched and nodded. “A little.” 

“You okay?” 

“I'm awesome,” Dean said, meeting Castiel's eyes. “That was awesome. Are you okay?” 

Cas pressed his fingers to Dean's lips before bringing them to his own mouth. “I'm good. You were beautiful.” 

Benny's voice drifted over. “You guys go ahead and sleep here tonight. We'll chat in the morning.” 

“Thank you, Benny,” Cas called out. He leaned down to kiss Dean's forehead. “Sleep now, love.” 

Dean did just that.


	6. See If I Can Stand It

**Summary for the Chapter:**

> “Now what did you say to make him pout like that?” Benny leaned against the frame of the open door. 
> 
> Jimmy's pout increased. “Castiel won't share his toys.” 
> 
> Benny's booming laughter filled the room. “You poor thing.”

Dean jolted as pain brought him awake. 

He hissed as he quickly rolled onto his side. His ass was on fire. 

Castiel's sleepy chuckle came from the pillow next to his. “Sore?” 

Dean grumbled and rolled onto his stomach. “Shut up.”

Cas propped a hand under his head. “Seriously though. You're okay?” 

“My ass hurts but last night was amazing.”

Cas worried his bottom lip with his teeth. “I didn't hurt you?” 

Dean leaned up and kissed his fiance gently. “You hurt me exactly as much as I wanted.” 

A brief knock was the only warning they got before Jimmy sauntered into the room. “Yo, Adonis. How's the rear end situation this morning?” 

“Dick. You know it's sore.”

Jimmy wiggled a jar in his hands. “I come bearing gifts. I'd offer to put it on you myself but I like having fingers.” He tossed the jar at Cas who fumbled it before letting it fall to the bed. 

“Nice catch, babe.” Dean grinned and snuggled back into the pillow. He yelped when Cas laid a playful spank. 

“Be nice,” Castiel growled. 

“Is this foreplay? I'm totally grabbing a seat if it's foreplay.” Jimmy looked around the room as if searching for a chair. 

Cas rolled his eyes as he reached for the waistband of Dean's underwear. “Is it okay if Jimmy takes a peek with me? He knows what to look for in terms of day after damage.” 

Dean grunted his assent. Whatever made Castiel more comfortable. He squirmed as cool air hit his sensitive ass. 

“Looks good, brother.” Jimmy rubbed a small circle on Dean's mid-back. “The welts will go down by the end of the day. No bruising that I can see. You'll be sensitive, Adonis, but nothing terrible.” 

Dean sighed with relief as cool cream was rubbed into his skin. “What's that? It smells funny.” 

“Arnica cream,” Jimmy answered. “It's good for bruising typically but it's just soothing as well.” 

Dean hummed as Cas finished rubbing down his ass and pulled up his boxers. 

“If you're finished, Benny wanted me to invite you to breakfast.” Jimmy took the jar from Cas and set it on the table by the bed. 

“Bring me pants,” Dean mumbled.

Jimmy scoffed. “And miss your naked chest walking through the room? I think not.” 

Dean smirked and pushed his upper body away from the mattress with a small groan. His back and shoulders flexed with effort. He pressed into a modified pushup position before kneeling up and stretching his arms over his head. 

Jimmy watched with rapt attention. “You're sure you don't want to share, Castiel?” 

“Quite,” Cas answered. “Besides, you don't fuck the same guy twice.” 

“I would make an exception,” Jimmy sighed. 

“No.” Cas climbed out of bed and collected his and Dean's discarded clothing. 

“Now what did you say to make him pout like that?” Benny leaned against the frame of the open door. 

Jimmy's pout increased. “Castiel won't share his toys.” 

Benny's booming laughter filled the room. “You poor thing.” 

“Do I smell bacon?” Dean asked as he finished dressing. 

“Do you know me at all?” Benny asked with mock offense.

Dean clapped a hand on his shoulder. “You've been surprising me lately.”

The four men made their way to the kitchen and settled at a table laden with bacon and waffles. 

After a minute, Benny turned to Cas. “How are you boys doing after last night?” 

“Dean is a bit sore but that's to be expected. I'm less nervous now.” 

Dean watched their conversation to see if they'd address him directly but it seemed to be Doms only so he shrugged and resumed digging into his waffles. 

Jimmy brushed a foot against Dean's under the table so he wouldn't feel so left out. The gesture brought a warm grin to Dean's face. 

“I'd like to have you over a few more times until you're totally comfortable,” Benny was saying. “Work with some other implements to see what your sub likes best.” 

Cas nodded as he swallowed. “That would be best.” 

“Did he discuss my possible involvement with you?” Benny asked. 

Cas wiped his mouth on a napkin. “No, but Jimmy alluded to as much.” 

“How do you feel about that?” 

Cas sighed. “Uncomfortable. But I know it's necessary when we move into more intense areas. Especially leather straps.” 

“Is that what. . .” Benny began. 

Cas closed his eyes and nodded. “I haven't picked one up since.” 

Benny narrowed his eyes. “You're sure you want to go through with it? You can always make it a hard limit for yourself.” 

Castiel's expression hardened. “I don't want to be afraid. It's holding back my relationship with Dean and it's something I'm able to work through.”

“Hey,” Dean interrupted. “Our relationship is just fine. If you never spank me again we'll be just fine. Don't think I'm only with you for the Dom/sub stuff. I'm not. I love _you_ , you idiot.” 

Benny turned to Jimmy and stage whispered, “Are they always so sappy?” 

“Yep,” Jimmy whispered back. “It's gross.”

“Oh fuck you.” Dean threw a piece of bacon at Jimmy's face. 

Jimmy thrust out his lower lip in a pout. “Don't tease me, Adonis.” 

“Yeah,” Benny added. “That's my job.” 

Dean groaned. “Gross.” 

“Don't start. We all know how much you enjoyed my working on Jimmy at your place. I've just been polite enough to refrain from mentioning it.” Benny raised an eyebrow in Dean's direction. 

“I'm not that polite!” Jimmy cackled. 

Dean flushed. “Dammit.” 

“Dean has a bit of an exhibitionism kink. I wouldn't be surprised if that extended to light voyeurism as well.” Cas rubbed his lips in thought. 

“What the hell, Cas?” Dean said. 

Castiel sighed. “Dean. If we can be honest about our relationship and kinks with anyone it's going to be Benny and Jimmy. At least they'll understand and not judge us.”

Dean scrubbed his hands over his face. “I'm still adjusting to my boss knowing I get off on getting my ass beat.” 

Benny shrugged. “Just don't go braggin' about it at work and we'll be fine.” 

Dean shuddered. “I'm sure I wouldn't like the thrashing I'd get from Bobby if that happened.” 

Cas cleared their plates, despite Benny's objections. 

“We should head out,” Jimmy said with a stretch. “Can I stay with you guys for a few days?”

“Of course, man.” Dean smacked his arm. “You're always welcome.” 

“Moose won't mind?” 

Benny barked a laugh. “Moose. That's perfect.” 

Dean shrugged. “He has his own room.”

“Are you having issues with your roommate?” Castiel asked. 

Jimmy sighed. “He keeps hitting on me and 'accidentally' walking in on me in the shower. I'm kind of over it.”

Dean and Cas exchanged a glance before Cas nodded. 

“Why don't we just load up your shit and you can move in with us? Sam isn't there half the time so it wouldn't feel like four people,” Dean suggested. 

“It's just temporary,” Jimmy warned. 

Castiel rolled his eyes. “Just accept the kindness and get your ass out to the car.” 

Jimmy blew a kiss in Benny's direction before skipping out the door.

**Notes for the Chapter:**

> Help me, creative people...you're my only hope. 
> 
> I'm not sure where to take this piece of the verse. Let's make the next chapter fun smut. What do you want to see our boys get down to next?


	7. Chapter 7

**Summary for the Chapter:**

> Dean heard the slight squeak of springs as heavy male bodies crashed into the mattress. A bitten off gasp sounded like a gunshot to Dean's ears. 
> 
> The whimper that came from Dean's throat was followed by an interested hum from the man sharing his bed. 
> 
> “He knows you can hear him,” Cas whispered, leaning into brush his lips against Dean's ear. “He wants you to hear it.”

**Notes for the Chapter:**

> Taking a suggestion from the comments here. This chapter is a little different. Short but put out fast. The next one is going to be a doozy.

Dean put the key into the lock and paused when a loud, feminine squeal came from behind the door. He smirked as he pushed it open to feet scampering down the hall. 

“We'll just wait here,” he called toward Sam's slamming door. 

It didn't take long for the frustrated and rumpled couple to emerge, glaring at Dean. 

“Don't look at me like that. Don't you have a roommate free apartment?” 

“We were celebrating and got carried away.” Jo pulled her tangled hair into a quick ponytail. 

“Celebrating?” Dean asked. 

Sam took a deep breath. “I'm moving in with Jo.” 

Dean held up a hand. “Which one of you suggested it?” 

Sam flushed. “I don't see why –”

“Sammy,” Dean interrupted. 

Jo smirked. “I did.” 

Dean wordlessly held out a hand in Castiel's direction. Cas grumbled as he pulled out his wallet and placed a bill in Dean's palm. 

“You were betting on this?” Sam sounded outraged. 

“Yup,” Dean said. “And Jo owning your balls just made me ten bucks.” 

Jo put her hands on her hips and glared. “You only put ten bucks on it?” 

Sam put his hands over his face. “So I guess you're okay with me moving out.” 

Dean opened his mouth but Cas got there first. “We are pleased that you're happy Sam.” 

“Do I get Moose's room or Adonis' old spot?” Jimmy asked. 

Dean shrugged. “Whichever you want I guess.” 

Sam put a hand on Jimmy's shoulder. “I'd recommend the one at the end of the hall. Thin walls.”

Jimmy's eyes sparkled. “And if I want to hear things?” 

Sam shuddered and turned to Jo. “That's our cue.” 

Jo grinned. “I like him.” 

Sam ushered her out the door, pausing only to make plans for a group dinner the next weekend. 

The men loaded Jimmy's suitcases into Dean's old room. It didn't take long for them to unpack everything and get Jimmy settled in to his new space. 

Jimmy stretched and checked the clock. “Bed time!” 

“Really?” Dean asked. “It's early.” 

Jimmy turned his head toward Dean with a grin. “Not all of us went to bed at a reasonable hour last night, Adonis. Some of us were up all night long. More than once.” 

Dean groaned and left the room, grumbling about lack of boundaries and how this was a terrible idea. 

Cas and Jimmy exchanged a glance before chuckling. 

Things were going to be interesting.

* * *

Dean's eyes flew open in his dark room. He lay still, trying to figure out what had pulled him from sleep when he heard footsteps in the hall. After taking a few days to settle in, Jimmy had gone to the club. Dean wasn't used to hearing someone enter the apartment in the middle of the night yet so it must have been the front door that woke him. 

Two sets of feet walked past his cracked bedroom door. Why hadn't they shut it all the way? 

Dean heard a groan and Jimmy's answering chuckle. The sounds were louder than he would have expected from the end of the hall . . .

Realization washed over him.

Jimmy hadn't shut his door. 

Dean heard the slight squeak of springs as heavy male bodies crashed into the mattress. A bitten off gasp sounded like a gunshot to Dean's ears. 

The whimper that came from Dean's throat was followed by an interested hum from the man sharing his bed. 

“He knows you can hear him,” Cas whispered, leaning into brush his lips against Dean's ear. “He wants you to hear it.” 

Dean bit into his lower lip. 

Cas clucked his tongue. “Now now, what have I told you about hiding those pretty noises from me? What's your safeword, Dean?” 

“Red to stop, yellow to slow down.” 

“Good boy.” He trailed kisses down the length of Dean's body. Giving a soft bite for every sound he pulled out of the man spread across the bed. 

Dean let out a breathy groan when Cas licked across the head of his cock. 

Cas hummed as he nuzzled the side of Dean's length. “You only fucked him, right?” 

Dean's answer was cut off by a muffled moan from the other room. Jimmy's. Jimmy with cock in his mouth most likely. 

Cas kissed the inside of Dean's thigh. “So you don't know what he looks like right now? His lips stretched as he sucks his partner down. I guess you could always just look down . . .” He trailed off before taking Dean into his mouth. 

Dean glanced down his body to see Castiel looking up at him with the wide eyes he'd come to associate with his twin. “Oh fuck.” 

The men down the hall must have heard him because he heard an unfamiliar gasp followed by a whimper that was undeniably Jimmy. 

The squeaking of mattress springs developed a rhythm. Dean panted as Cas began bobbing in time to the beat being laid by the other couple. Dean glanced down again to see Cas stripping is own cock to the same rhythm. 

Dean groaned as his balls drew tight. Answering moans rang out around him and pushed him closer to the edge. 

He exploded in Castiel's mouth with a shout and a thrust. Cas moaned as he swallowed before kneeling up to continue fisting his own cock. It didn't take long for come to splash on Dean's softening dick, Castiel's soft groan preceding a pair of cursing cries from the other room. 

Cas was cleaning Dean with wet wipes from the side table when Jimmy called out, “You're welcome.” 

“Fuck you,” Dean yelled back playfully. 

“Already did,” came an unfamiliar voice. 

Cas snorted a laugh. “You're all impossible.” 

“Love you too, brother.” 

“Brother?” the unfamiliar man asked. 

There was a moment of silence before the same voice groaned out, “Oh my god, two of you?” 

Dean and Castiel laughed until their sides ached. 

* * *

Dean sipped his coffee the next morning while Cas made breakfast. Their heads turned as Jimmy and his mystery man made their way to the front door. A few mumbled words and a kiss later, Jimmy shuffled into the kitchen. 

“No morning after?” Dean asked. “I made coffee.”

Jimmy yawned and shook his head. “Breakfast with the family implies commitment.” 

“Fucking with your family down the hall doesn't?” Cas mused from his spot at the stove. 

Jimmy shot Dean a wicked grin. “Nope.” 

“Does your mystery date know you won't be seeing him again?” Dean asked. 

Jimmy nodded. “I was clear before I brought him back. He was looking for the same thing. It was perfect.” 

“Then why do you look disappointed?” Dean said gently. 

Jimmy frowned. “Being with Benny has made me miss that kind of thing.” 

“So why not just hook up with Benny?” Dean took a long gulp of his coffee. 

Jimmy sighed. “I don't want to talk about this anymore.” 

“Fair enough,” Castiel interjected with a hand on Dean's shoulder. “Eggs?”

**Notes for the Chapter:**

> Reminder that I take kink suggestions!


	8. Chapter 8

**Summary for the Chapter:**

> “Hmm,” Cas hummed. “And they're beautiful aren't they? Their passion. Their heat. Their connection. It's wonderful to watch.” He tugged Dean's hair until the submissive looked up. “I do not doubt your love for me, Dean. Do you understand?” 
> 
> Dean was unable to nod with his head tugged back so he opted for a slow blink and a hoarse, “Yes, sir.”

**Notes for the Chapter:**

> So...that happened. Shit.

“So he finally moved out?” Benny said to Dean during one of their daily lunches. 

Dean bit into his burger and grinned. “Yep. Jo finally made him.” 

“What's the plan then? Can you and Cas afford the place yourself?” 

Dean shrugged. “Jimmy's still staying with us for now. We've got time left on the lease so it's what works for now.” 

“Any plans for the empty room?” 

Dean pursed his lips. “It's a guest room right now but the only guest we ever had stay was Jimmy so it's not being used.” 

They ate in silence for a bit longer before Dean asked, “Where'd you get that X-thing?” 

“Saint Andrew's Cross? Ordered it off the internet.” 

Dean barked a laugh. “Of course you did. The other pieces too?” 

Benny nodded. “All except the custom bed frame. I made that myself.” 

Dean hummed a thoughtful sound and munched a fry from his tray. 

“I wouldn't recommend turning that spare room into a playroom, hoss. The noises would scare your neighbors.” 

Dean visibly deflated. Damn Dom senses knowing what he was thinking. 

Benny smirked. “You can use mine any time. All you gotta do is ask and clean up when you're done.” 

“Got any plans for tonight?” 

Benny chuckled. “Not a thing. Just bring Jimmy and we're square.” 

“What's the story there, with you two?” 

“Nope, not my place to tell his secrets. You want 'em, you drag 'em out of him yourself.” 

Dean groaned and threw his balled up wrapper at Benny's face. 

* * *

Dean and Cas met Jimmy at Benny's later that night. 

Once again, Jimmy showed his comfort of Benny's home by letting himself in without knocking. “It's a habit from when we scened regularly,” he'd explained. 

Benny walked up to where Jimmy knelt next to the couch. Dean instantly felt the difference in the air and straightened his own spine. Cas ran a comforting hand down the back of his neck but obviously felt the shift as well. 

Jimmy fluttered his lashes and peered up at Benny with a demure grin. “Are we playing tonight, sir?” 

Benny held out a hand for Jimmy to take. When he'd pulled the other man to standing, he leaned in and whispered something that made Jimmy whimper and pin Dean with a heated look. 

Dean swallowed hard and squirmed. He glanced up at Cas who was watching him with an amused smirk. 

Benny pulled Jimmy along while the other couple followed in silence. Cas kept his hand at Dean's nape for the duration of the walk down the hall. 

Once inside the playroom, Cas pushed Dean to kneel on a pillow in a corner. Dean shifted until he got comfortable, his cock pressing painfully against his zipper. 

Jimmy stripped his clothing provocatively, taking time to peel each piece from his body, never breaking eye contact with Benny. The larger man watched with an approving gaze as each bit of skin was revealed. 

Dean skirted his glance when Jimmy shoved his underwear down until he was unabashedly nude. He couldn't help but look back when the sound of a moan was swallowed by a rough kiss. 

Cas stroked a hand through Dean's hair. “I don't mind if you look, gorgeous boy.” 

Dean flushed. “That's your brother.” 

“Hmm,” Cas hummed. “And they're beautiful aren't they? Their passion. Their heat. Their connection. It's wonderful to watch.” He tugged Dean's hair until the submissive looked up. “I do not doubt your love for me, Dean. Do you understand?” 

Dean was unable to nod with his head tugged back so he opted for a slow blink and a hoarse, “Yes, sir.” 

He was released as buckles jangled in the silence. Jimmy stood spread across the Saint Andrew's Cross and Dean let out a small whimper of jealousy that made Cas growl low in his chest. “Next time, sweetheart.” 

Dean bit his lip as Jimmy canted his backside out, begging for what he knew was coming. Dean's ass tingled in sympathetic anticipation. 

Benny started off harder this time. The leather bound paddle smacked Jimmy's flesh with unerring accuracy, never hitting the same place twice. Each slap was followed by a sound from Jimmy. Dean's cock jumped with every gasp and moan. 

When Jimmy's rear and back of his thighs had turned red, Benny tossed the paddle on the floor and lubed his fingers. Dean choked on a gasp when Jimmy threw his head back as Benny started opening him up. 

“Stand up,” Castiel instructed. 

Dean obeyed instantly, never taking his eyes from the scene playing out before his eyes. 

“Strip.” 

Again, Dean didn't hesitate. He pulled off his clothes with no seduction in mind, just blanket obedience to his Dom. 

When he was naked, Cas ran light fingernails over his exposed skin. Dean hissed as the sensation overwhelmed him. Jimmy's answering groan heated his blood even more. 

“Do you want a spanking, gorgeous?” Cas purred. 

Dean nodded fervently. 

“If I spank you, I'll have to stop before you get too deep because I want that huge cock in my ass tonight.” 

Dean moaned in response, no longer feeling weird about his friend being in the same room. 

“Please,” he begged. 

“Over the side of the bed.” 

Dean fought the urge to run into place. Dimly, he heard buckles being undone behind him but didn't think anything of it until Jimmy laid on the mattress beside Dean. 

Jimmy winked as he got into position, bent over the bed with his hands above his head. 

Benny's voice came from behind them. “Safewords, boys.” 

“Red to stop. Yellow to slow down,” they repeated in unison. 

A breath later, Dean gasped when pinpricks of pain rained down on his ass. Each blow of the flogger lighted a dozen sparks across his skin. The pain wasn't intense, but it was widespread. The strips of leather could cover more places at once. 

He was instantly addicted. The flogger immediately falling into second place for his favorite impact play implement, the first being Castiel's bare hand. 

At the same time, Jimmy hissed and groaned. “Fuck, that's good.” 

A handful of blows later and there was a lull in the activity. Jimmy glanced behind Dean before reaching out to take the green-eyed man's hand. 

Dean laced their fingers together, feeling more grounded. 

A sharp pain lanced through his thoughts. “Holy fuck me.”

The heat took longer than before to head to his groin, and the overall feeling was more intense. 

“Yellow,” he choked out, feeling horribly overwhelmed.

“Stop,” Cas said. 

Stop? Stop what?

Cas leaned until his face was level with Dean's. “Okay, baby. You did well. Are we okay to do more?” 

Dean nodded. “Just not whatever that was again.” 

“Understood.” Cas kissed his cheek and stood back up. “Up on the bed, on your back.” 

“Other side, cher,” Benny instructed. “Same position.” 

Jimmy and Dean both scrambled to get where they'd been told, shifting as sensitive skin hit fabric. They reached at the same time to link hands once more. 

Benny moved Jimmy's feet so his legs were spread open wide before reaching in and checking to make sure he was stretched fully. 

Cas licked a hot stripe up Dean's flushed cock before taking it deep into his throat. Dean groaned loudly, his muscles shaking from the need to thrust into the wet heat. 

Benny unzipped his pants and removed himself from the opening. Dean only saw out of the corner of his eye, most of his attention directed at his now naked fiance climbing on top of him. 

Benny sank into Jimmy with a satisfied sigh at the same time that Castiel lowered himself onto Dean with a whispered, “fuck yes.” 

Dean felt Jimmy's grip tighten briefly as his body accepted the intrusion. Dean let the pain ground him for a second and barely resisted coming instantly inside Castiel. 

Benny began thrusting. From the sounds Jimmy was making, the man was hitting his prostate each time. 

Castiel moved his hips and squeezed around Dean, causing the sub to cry out and hold his breath. He was ready to explode. When Castiel began bouncing up and down with hard drops, Dean wasn't sure he'd last.

Jimmy wasn't faring much better. His breathing had gone wonky and Dean recognized it from their bathroom tryst. He was just as close as Dean. 

Jimmy's head snapped over and his gaze met Dean's. Dean felt an odd tingle in his gut as they stared at each other.

When Jimmy's eyes darted down to Dean's mouth, Dean couldn't stop the whimper of confused want that skittered across his skin. 

Cas let out a thoughtful hum before beginning to stroke himself. It only took a few strokes before he came across Dean's stomach. The rhythmic tightening causing Dean to come with a yell. 

Jimmy's eyes shut as he finished on a silent scream, Benny's soft grunt the only sign he'd climaxed as well. 

Each Dom cleaned their sub before themselves and then everyone dressed, or stripped, to underwear. Everyone had a round of juice from a hidden fridge Dean hadn't seen previously.

Dean felt Jimmy press a soft kiss to his bare shoulders before rolling into Benny's embrace. Cas placed his fingers on Dean's lips before bringing them to his own mouth. Dean repeated the ritual, remembering their first experience together with a soft smile. 

His head lifted to ask Cas a question about earlier but he was silenced with a kiss. 

“Sleep now, we'll talk tomorrow.” 

Feeling satiated and comfortable, Dean settled into the mattress surrounded by three of the men he trusted most in the world.

**Notes for the Chapter:**

> _Author glares at characters_ This is not that kind of fic and Cas doesn't share. STOP IT.
> 
> Rest assured, this is not turning into a Jimmy/Cas/Dean fic.


	9. Chapter 9

**Summary for the Chapter:**

> “Last night. . .” Dean hesitated, unsure of where to begin.

**Notes for the Chapter:**

> I know this is really short but I realized what the moment was and wanted to make sure Dean and Cas were okay! I hope this helps ease your minds as much as it did mine!

Dean woke up curled against Castiel's chest. He rolled over and stretched, happy to find the rest of the bed empty. 

“Good morning,” Cas mumbled. 

Dean laid on his side and kissed Cas lightly on the lips. “Can we talk or do you need coffee first?” 

Cas scrubbed his eyes and yawned. “We can talk while we have some alone time.” 

“Last night. . .” Dean hesitated, unsure of where to begin. 

“You safeworded.” 

“I'm sorry,” Dean whispered. 

Cas tipped his chin up. “No. I'm so fucking proud of you for knowing your limits and keeping me informed. It only strengthens our relationship and solidifies my trust in you.” 

Dean nodded. That made sense. “You said 'stop' though.” 

Cas raked his gaze across Dean's face for a second before explaining, “I was talking to Benny.” 

Dean's eyes flew wide. “You mean. . .” 

“He used the leather strap on you. I wanted to see how you'd react but I didn't feel comfortable doing it myself.” 

Dean shuddered. “I'm not sure I like it.” 

“That's completely fine. If you never want to do it again, we can mark it as a hard limit for both of us.” 

“I think we should.” 

Castiel nodded. “You seemed to enjoy the flogger though.” 

Dean flushed and buried his face in Castiel's chest. “I did. That was nice.” 

Cas carded a hand through Dean's hair. “Anything else you need to talk about before we get up for the day?” 

Dean sighed. “There was a moment, with Jimmy. I feel weird about it.” 

Cas hummed. “I was waiting for you to mention that.” 

“You noticed it?”

“I did.”

“I'm sorry.” 

Cas tugged Dean's head back so they could make eye contact. “I'm not angry, Dean.” 

“I don't know what happened,” Dean whispered. 

Cas kissed Dean softly. “Are you attracted to my brother?”

“Yeah,” Dean admitted with a shrug. “I mean, he looks just like you. But I'm not in love with him.”

Cas chuckled. “I know, sweet boy. You'd be lying to yourself if you denied having a connection to Jimmy. There are deep emotions there. There is love, but it's different from what we have. You understand each others need to submit. And he trusts you. It's not every day Jimmy connects with someone like he has with you. It's beautiful. Your comfort with each other pleases me. I know you'd never cheat, Dean.”

Dean chewed his bottom lip. “He acted like he wanted to kiss me.” 

Cas nodded. “And in that moment he probably thought he did. You did as well. My guess is you feel the emotional connection to Jimmy and you had trouble separating that from your attraction to him. Just for a second, mind you. But I can see how that would bother you.” 

“So what do we do now?” 

Cas shrugged. “That's up to you and Jimmy. You need to establish your relationship boundaries yourself. I won't force anything on you.”

Dean sighed. “Okay. I guess I should talk to him.” 

“Your favorite thing.” 

Dean wrinkled his nose. “I know, right? Ugh.” 

The door opened and Jimmy walked in wearing low slung jeans and his shirt unbuttoned. “Oh good, you guys are up!” 

“Barely,” Cas said with a yawn. 

Jimmy sat at the far corner of the bed from the couple. He cleared his throat. “So, Adonis. . . about last night. You know I would never . . .”

Dean patted the bed next to him. “Come here, dude.” 

Jimmy moved cautiously. He crawled across the bed and settled in alongside Dean, his body language strained and stiff. 

Dean huffed and threw an arm around the dark haired man. “Cas has a theory and it explains a lot.”

Jimmy looked over at his twin. “Yeah?” 

Cas smiled. “I'm not angry. I know you two are attracted to each other and that you have a connection. I'm not blind. But I also trust both of you. As long as you keep it to light flirting and longing glances I'm fine. Seeing you two trust and find comfort in each other makes me happy because we're a family.”

Dean kissed the top of Jimmy's head. “Okay?” 

Jimmy threw an arm over Dean's torso to grip Castiel's hand. “Thanks, bro.” 

“Where's Benny?” Dean asked. 

“Work,” Jimmy answered. “I think. Or grocery shopping. I was kind of in an orgasm haze when he told me.” 

Castiel rolled his eyes. “I guess we should head home then.” 

Jimmy picked at imaginary lint on the blanket. “If it's okay with you guys, I'm going to stay here for a few days.” 

“Whatever you want,” Dean said quickly. 

Jimmy laughed. “You're planning all the sex you can have while you have the apartment to yourselves, aren't you?” 

Dean looked over at his fiance. “You know, I am due some vacation time.” 

“Sounds like a plan.” Cas stretched with another yawn. “I need caffeine.” 

Dean threw his arm out in the general direction of the room. “Pants!” 

“Like hell!” Jimmy said. 

“Didn't get enough of a view last night?” 

Jimmy placed a hand over his heart. “Never, Adonis.” 

Dean shoved him. “Shut up and bring me pants.” 

Jimmy faked a put-out sigh. “Fine.” 

Cas rolled his eyes. “I can get my own clothes.” 

“Good,” Jimmy said. “Because I'm sure as fuck not doing it for you.” 

Cas snagged a pillow and threw it at his brother. 

* * *

Dean flopped on to his mattress, feeling oddly drained despite sleeping the night previously. 

“Why am I so fucking exhausted?” 

Cas sat next to him. “Endorphins. Last night took a lot out of you. The worrying about the whole Jimmy thing didn't help.”

Dean sighed and burrowed under the blankets. “We're good though?” 

Cas kissed his throat. “We're fine.” 

Dean peeked out of one eye. “Can I make a request then?” 

“Of course you can, gorgeous boy.” Cas frowned. 

“Can we. . . cool it on the spanking stuff for a while?” 

Castiel's frown deepened. “Are you not enjoying it?” 

“No!” Dean barked out. “It's not like that at all. I just miss the other stuff is all. I want to try something new.” He flushed as he let the last part turn into a mumble in the pillow. 

Cas grinned. “Something new?” he purred into Dean's ear. “I think I can work with that.”

**Notes for the Chapter:**

> What new kink would you like to see? Hmmm
> 
> Pet play? Rope? Ice? Wax? Food? Something else? I take kink suggestions!


	10. Chapter 10

**Notes for the Chapter:**

> Sorry for the late and short chapter. I'm moving so I've been packing and readying the house!

Dean woke up naked. 

Which was interesting considering he didn't go to bed naked.

He was also alone in bed so that made the whole nudity thing even more confusing. Naked was understandable if Cas did it to suck his dick but just because? Something was up. He could only hope it was something kinky. 

He got out of bed and strolled to the dresser where he discovered his sock and boxer drawer completely empty. With a smirk, he opened his panty drawer. Yep, fully stocked. 

All right. That was obvious enough. 

Dean slipped into his pink satin bikini cut panties. They were an upgrade from the previous pair but looked quite similar. 

He walked into the kitchen. “Babe?” 

Silence. 

Okay, something was definitely going on. . .

A brightly colored card caught his eye. That's when he noticed an array of items sitting on the kitchen table. 

He glanced around before picking up the card. 

_Dean,_  
I endeavor to introduce you to more kinks. Therefore, I've devised a little activity.  
Each item represents something we have not explored yet. Each card accompanying the item holds a brief explanation of the activity.   
If you do not want to explore something, please place the card facedown and ignore the item. If you find something you wish to try, please take the item to the living room and set it on the coffee table. I will return at nine o'clock to go over your choices with you.   
Love,  
Cas 

Dean's heart sped up as he glanced at the clock. Thirty minutes. Cas must have left when he heard Dean rummaging around in their room. 

He took a deep breath and surveyed the items on the table. 

A thermometer sat next to a large, studded collar. Above those was a coil of rope and a can of whipped cream. 

He smirked. At least a couple were obvious. 

Sure enough, when he picked up the card in front of the whipped cream it read “Food play” with nothing else; not that Dean needed more of an explanation. 

The card with the rope read “Rope Bondage” with notes of wearing it during sex or how certain styles can be worn under clothing as a secret public play aspect. 

His head tilted to one side when he reached for the card with the thermometer. Medical kink maybe? 

Nope. “Temperature play.” Apparently there were low temp candles for wax play. Huh. Interesting. 

The collar was the last card that he checked out. “Pet Play.” Dean's face flushed. He hadn't put that down as a hard limit originally but hadn't shown interest in it. The idea of crawling on the floor acting like an animal was . . . strangely intriguing and he instantly felt a wave of embarrassment at the thought. 

In the end, he grabbed all four items and made his way to the couch. A bowl of fruit was laid out, and still cold, next to an open box on the table. Cas really did think of everything. 

The time passed more quickly than Dean would have expected. He'd eaten half the fruit when he heard a key in the lock. 

His head whipped around as a flush worked over his body. 

Cas strolled into the room with a wide grin. “You are so fucking sexy.” 

Dean swallowed. “Sitting in my panties eating fruit?” 

“Always,” Cas whispered as he brushed a kiss against Dean's mouth. “So, show me.” 

Dean reached into the box and withdrew the whipped cream first. “I'm not sure how sexy this would be but I love food and I love you so. . .” 

Cas chuckled. “Food play tends to start off sensual and end up in dirty amusement. It's right up our alley.” 

Dean pulled out the coil of rope next. He figured he'd go in order. 

“Rope interests you?” Cas asked. 

“I liked being cuffed to the bed and this is an upgrade on that, right? Plus wearing it in public sounds interesting; like I'd be able to feel you when I was at work or the store.” 

Cas nodded. “That's part of the appeal, yes.” 

Dean took a deep breath and handed him the thermometer. “The idea of wax freaks me out but I trust you. If you think it's something I'd like to try, then I'll give it a go.” 

“We'll talk about it more before we do it then.” 

Dean chewed his lip and looked at the last item in the box. He knew he could change his mind and Cas wouldn't be upset. He could back out and pretend he hadn't even considered it. 

But. . .

Cas startled as the collar landed in his lap. He raised an eyebrow. “This surprises me.” 

Dean could feel his cheeks heat. “I don't know. I thought about it and something appealed to me. I feel silly.” 

Cas captured his chin and raised his face. “You have nothing to be embarrassed about, gorgeous boy. If you want to give it a go then that's what we'll do.” 

“What pet would I be?” Dean asked at a whisper. 

Cas tilted his head. “That's for you to decide. I won't assign you something. Generally, it's an animal you feel close to in some way. Maybe you had a pet as a child or a favorite animal at the zoo or even just see certain traits in yourself. It's entirely your choice.” 

“Can I think about it?” 

“Of course. We won't do anything until you're ready and we've discussed it. Pet play takes a bit more planning on my part to make sure you have a genuine experience while also having fun.” 

Dean bit the corner of his mouth. “Would we have sex while I'm. . . you know?” 

Cas narrowed his eyes and put on his thinking face. “Not if it makes you uncomfortable.” 

Dean sighed. “Okay. More to think about I guess.” 

“Would you like to try food? You seem like you need something lighthearted.” 

“Please!” 

Cas grinned. “Go to the extra room and wait for me. . . naked.” 

Dean immediately complied. He tossed the panties into the hamper on his way through. 

Cas had changed the sheets on the bed. Sam's old sheets used to stay on it but Cas had put a worn out set on instead. 

“All the better to spill shit all over,” Dean mumbled. 

Cas entered with a medium sized box covered with a lid.

Dean eyed it. “What's in the box?” 

Cas rolled his eyes. “Sit against the headboard and keep the blindfold on hand.” 

He waited until Dean had followed through before continuing. “We're going to play a game. I'm going to spread something on my torso. You not only have to find it and lick it off in thirty seconds, blindfolded, but you have to guess what it is. Each correct find and guess earns you a point; otherwise the point goes to me.” 

Dean raised his eyebrows. “If I win?”

“You can choose the next kink we explore and any specific parameters you wish.” 

“If you win?”

Castiel's voice dipped lower. “No orgasms for the next 24 hours, but that won't stop me from teasing you.” 

Dean groaned and tipped his head back. “So a day of orgasm denial?” 

“Correct.” 

Dean wiggled in his seat. “Let's get started. I want to get my mouth on you.” 

Cas laid down next to Dean and guided the man to straddle his waist. “Also, no hands.” 

Dean nodded as he slipped the blindfold into place, determined. “Got it.” 

Cas swiped the first substance onto a collarbone with a grin. He pressed the button on his phone to activate the timer function as he said, “Begin.” 

Dean leaned onto his hands and licked a slow trail up Castiel's chest. He dragged the tip of his tongue carefully across the skin, staying aware for changes in taste or texture. It didn't take long for him to run nose first into a dollop of whipped cream. 

He scrunched up his face as he licked what was left into his mouth. “Whipped cream.” 

Cas laughed as he clicked the button to stop the countdown. “Correct.” 

“I think I inhaled some.” 

“Stop being a baby.” 

Dean smacked blindly, hoping to hit skin. “Dick, it went up my nose. Hand me a towel.” 

“Fine,” Cas sighed, pretending to be put out by the request. 

Dean sat back on his heels and wiped his face. He dropped the towel onto Castiel's chest and waited. 

He could feel as Cas shifted around, putting the towel up and a new substance onto his skin. 

“Are you ready, your highness?” Cas teased. 

“You're just mad that I got a point.” 

Cas pressed the button to start the timer. “Go.” 

Dean repeated his path to the best of his ability. He licked in straight lines before switching to curving twists and bends. 

“Fifteen seconds.” 

Dean increased his speed slightly but continued hitting nothing but fresh skin. His hands twitched with the urge to swiped the areas he couldn't cover and then. . . 

“Time.” 

Dean sat up with a frown. “Fuck.” 

A sticky finger pressed between his lips and he licked the digit clean with a sigh. Caramel. Dammit. He'd missed the chance to lick up caramel. 

“One more, point determines the victor.” 

Dean nodded as he felt Cas clean up and get settled for the next round. 

“Go.” 

Dean changed his tactics a bit. Instead of light brushes with the tip of his tongue, he laved in long and wide stripes; letting the hot muscle trail over as much skin as possible with each pass. 

He moved in an up and down path until he hit a patch that felt slightly sticky. He quickly brought his tongue into his mouth and savored the flavor long enough to . . . 

“Chocolate.” 

Cas pulled the blindfold off. “Very good.” 

Dean beamed. “I won!”

Cas brushed a chocolate coated thumb against his lips. “You did. What would you like for your prize?” 

Dean chewed his bottom lip. “Can I think about it?”

“Of course you may.” 

Dean wiggled in place, noticing neither of them had gotten very hard. “We're not, um.” 

Cas gave him a comforting smile. “Sometimes a scene isn't about sex. It's about exploring different aspects of yourself or trying something new. Sometimes you'll need to learn a lesson of some kind in the future and I'll use a scene to help you.” 

“Like what?” 

Cas rolled his eyes. “Like patience and self control.” 

Dean took the opportunity to tickle his Dom until Cas threatened to throw him off the bed.

**Notes for the Chapter:**

> Which of the 3 kinks left do you want to see next?


	11. Chapter 11

Dean and Cas were lounging in front of some reality show when Dean came to his conclusion. 

“Let's just go through the kinks in the order I showed you. Would that be okay?” 

Cas kissed him gently. “If that's what makes you comfortable of course it's okay.” 

Dean felt a flush spread up his neck. “Can. . . can we try the rope?”

“Now?” 

Dean nodded. 

Cas hummed and traced his eyes across Dean's hopeful expression. “I believe I can do that. Wait here and remove your shirt.” 

Dean hurriedly stripped as Cas went to the bedroom. His heart sped up. He liked basic bondage and the idea of taking it up a notch, like they had with impact play, was appealing.

Castiel returned with two lengths, one blue and one black, of soft rope and a pair of scissors. “Stand up for me.” 

Dean obeyed, licking his lips in anticipation.

Cas looped the rope around Dean's ribs before tracing it up between his pecs. He repeated this on each side until a V fell between Dean's nipples with rope wrapping around his torso. Cas tied it off before running his fingers between the rope and Dean's skin. 

“Wrap your arms behind your back and grasp each elbow.” Cas reached for the next length of rope. 

Dean furrowed his brow as he focused on placing his arms in the correct position. He didn't feel much yet in the way of arousal but a strange calm was thrumming in his veins. 

Cas looped the rope around Dean's clasped arms. 

When the knot was tied off, the arousal set in. 

Dean was mostly immobile. He bit down on his bottom lip as he watched Cas walk a slow circle around him. 

“How does that feel?” Cas murmured. 

Dean swallowed hard. “It feels good.” 

Cas hummed. “On your knees.” 

Dean lowered himself, rocking slightly when he realized he didn't have his arms to steady his movements. 

Cas ran a hand through Dean's hair, tugging his head back. “How about I put those pretty lips of yours to work?”

Dean whimpered in response. 

Cas released his cock from his pants and pressed a thumb alongside Dean's lips. “You like that? All trussed up and helpless? You want to suck me, gorgeous boy?” 

Dean nuzzled up Castiel's length. “Please,” he whispered. 

Cas rubbed the head of his dick along Dean's mouth, leaving a streak of precome behind. “Open.” 

Dean opened his mouth and tipped his head back slightly so Cas could begin to thrust inside. After every few thrusts, Cas would pull back enough for Dean to give the head of his cock a firm lick. 

Dean groaned with each taste. His erection pounded behind his zipper and he whimpered with every move Cas made. 

Cas pressed slowly into Dean's mouth, allowing Dean to swallow around him. He pulled out on a husky groan. 

“Stand up,” Cas directed. “Bend over the arm of the couch.” He laid a few pillows down to make Dean more comfortable as he laid himself down. 

Dean spread his legs as Cas pulled his jeans off. Cas knelt down and grasped each cheek with a hard squeeze, making Dean cry out as a lick of pain went straight to his dick. 

Cas pulled Dean's cheeks apart and immediately licked hard on his exposed hole. 

“Oh fuck,” Dean exploded as he canted his hips back for more. 

Cas nipped a sharp bite where ass met thigh before returning to working his tongue into Dean. He pressed a finger in alongside his tongue and pressed right on Dean's sweet spot. 

Dean cried out, his breath coming in harsh pants. He wanted to reach back and hold himself apart or hold Castiel's hair. He wanted to fist his hands in the couch. But he was held immobile by the rope. 

“Please, please, please,” he begged. 

Cas continued to stretch Dean, using lube he'd stashed in his pocket. He stood and slicked his cock. 

There was no warning as he pushed into Dean's prepared body. Dean let out a low moan as he was filled with Castiel's hard, hot length. 

Cas rolled his hips and ground against Dean's prostate. He gripped the ropes encompassing Dean's arms and used them to pull Dean back as he thrust forward. 

“Can I come? Please? Oh fuck,” Dean babbled. 

“Do it,” Cas ground out. 

A few thrusts later had Dean coming with a loud shout. His legs shook as his cock pumped come onto the side of the couch. 

Feeling Dean squeeze around him pushed Cas over the edge. He came buried deep inside of Dean. 

The men stood and caught their breaths before Castiel undid the knots holding Dean's arms together. Dean stretched his arms out in front of him with a satisfied groan that quickly became a whimper as Cas pulled out. He ran his fingers across the marks tracing up and down his forearms. 

Cas cleaned him off with a damp rag before helping him stand. Dean looked at the mess on the side of the couch. “Oops, dammit. That'll be a bitch to clean.” 

Cas chuckled. “We didn't plan ahead.” 

“You did a little,” Dean answered. “Why the scissors?” 

“Safety measure. Just in case I need to get you out faster than I can untie my knots.” 

Dean nodded as he curled up on the couch. Cas covered him with a blanket and went to get juice. 

Dean drifted a bit, still aware of his surroundings but riding a slight endorphin high. 

“Drink for me,” Cas said as he sat down. He began untying the rope from Dean's chest. 

“Is this the kind I can wear under my clothes?” Dean asked, indicating the chest harness. 

“If you like.” Cas nodded and coiled the ropes. 

Dean sighed and snuggled into Castiel's embrace. “I like ropes.” 

Cas scratched light fingernails across the marks on Dean's arms. “What was your favorite part?” 

“I like it when you're in control.” 

Cas kissed Dean's forehead. “There is no higher praise for a Dom. Thank you.” 

Dean tilted his head back. “Thank you for letting me try new things and for not judging me.” 

Cas licked across Dean's lips. “It's fun for me too.” 

Dean scrunched his face adorably. “So temperature play next?” 

“That's what was on the list.” 

Dean bit the inside of his mouth. “Wax makes me nervous.” 

“You always have a safeword,” Cas reminded him. 

Dean felt a small wave of calm. “That's true.” 

Cas raked his fingers through Dean's hair. “Rest now. We don't have to worry about it yet.” 

Dean nodded and settled down into Castiel's lap. “I love you.” 

Cas smirked. “I know.”


	12. Chapter 12

**Summary for the Chapter:**

> “So are you going to tell me if this is Jimmy or Cas or do I have to guess. . . again?” Sam asked as he joined them. 
> 
> Dean raised an eyebrow. “Psh. Like Cas and I would be sitting on opposite sides.”
> 
> “Don't tempt me, Adonis.” Jimmy winked.

**Notes for the Chapter:**

> Sorry I've been gone! I'm trying to get everything somewhat updated. My laptop was out for repairs and some other stuff was going on but I'm BACK (at least until Nano)
> 
> Here's some fluff and humor! (Someone requested fluff and I thought it was nice to take a break from the sex sex sex I had going)

Sam kicked open the door. “Did I miss it?”

“Dude,” Dean exclaimed from his seat on the couch. “Chill. No. You're fine. Now calm down before you drop my beer.” 

Sam shook his head and made his way to the fridge. 

When the stars aligned and everyone had the same night off, the Winchester/Novak apartment was home to Sibling Night. 

Dean smirked and tossed a piece of candy into the mouth of the dark haired man sitting on the opposite end of the couch. 

“So are you going to tell me if this is Jimmy or Cas or do I have to guess. . . again?” Sam asked as he joined them. 

Dean raised an eyebrow. “Psh. Like Cas and I would be sitting on opposite sides.”

“Don't tempt me, Adonis.” Jimmy winked. 

The door opened to Cas and Anna carrying bags of snacks. 

“Sam!” Anna cheered as she dumped the bags on Dean's lap before pulling the younger Winchester in for a hug. “It's good to see you!”

Dean oofed as he adjusted to the sudden appearance of plastic bags. “Love you too, Anna.” 

Anna stuck out her tongue. “Always.” 

Sam laughed and reached to help Cas with the rest of the groceries. 

“So,” Anna said as she clapped her hands. “I had a stroke of brilliance.” 

“Aren't you supposed to go to the hospital after something like that?” Dean asked. 

Anna smacked his arm. “Dick. Shut up. I thought we could start having these at my house and invite our significant others. I mean, the rest of us deserve a chance to be disgusting to give you and Cas a break.” 

“And who, dear sister, am I supposed to bring?” Jimmy asked. 

“Benny,” she said flatly. “And don't give me crap about how you're not a couple. He's cool. You have chemistry. He's invited. Done.” 

Jimmy rolled his eyes and tossed a piece of candy to Dean. 

Cas plopped down on Dean's lap and greeted his fiance with a kiss. Anna curled up on a large pillow on the floor, leaving a small spot of couch for Sam. Jimmy caught Sam's eye and rubbed the open spot while waggling his eyebrows. 

Sam took a sip of his beer. “You're making me highly uncomfortable.” 

“Excellent!” Jimmy raised his drink in a toast.

Anna slapped his leg. “Be nice.” 

“Cas,” Jimmy whined, “she's hurting me again.” 

“I can see that,” Castiel replied. “I'd suggest retaliation but we both know she can kick your ass.” 

Anna batted her lashes at Jimmy with a saccharine sweet smile. 

Sam grinned and dropped onto the sofa inches from Jimmy. He threw an arm around the slighter man's shoulders and pulled him in close. Jimmy's response was to kick his legs up in Sam's lap and wrap his arms around the larger man like an octopus. 

Sam only shook his head and pulled an arm free to drink his beer. “So lovebirds, have you set a date yet? We need to know how long we have to put off getting you shit.” 

Dean and Cas looked at each other with wide eyes.

“We haven't really. . .” Dean began.

“. . . talked about it,” Cas finished. 

Anna tilted her head in contemplation. “Do I need to bring in you know who?” 

“Voldemort is not invited,” Dean deadpanned. 

Cas slapped a hand over Dean's mouth. “Do not tell Gabriel I need help planning this.” 

“The porn cousin?” Dean asked from behind Castiel's palm.

Cas nodded. “He'll make it some overly lavish affair that we'll both hate and annoy the hell out of you.” 

“He is invited though, right?” Jimmy asked. 

Cas sighed. “I was waiting until the last minute to keep his destruction minimal.” 

“How about April?” Sam suggested, steering the conversation back on track. 

Dean was nodding. “Spring is good. Before it gets too hot and the bugs get any ideas.” 

“Why would that matter? Are we doing it outside?” Cas inquired. 

Dean shrugged. “I thought we'd do a good old-fashioned Texas style barbeque for the reception. It'll give the guys from the garage something to do.”

Jimmy toasted into the air with his bottle. “I approve.” 

Anna tapped a finger against her lips. “I suppose that would work. What were you thinking for the actual event?” 

Dean held up his hands. “One thing at a time. We decided on a month and the reception theme. I'm doing planning for the night.” 

Sam whacked him with a pillow. Dean jostled, barely avoiding spilling his beer all over Castiel. 

“So what have you two been up to while I was at Benny's?” Jimmy asked, his smirk saying he knew the answer. 

Dean flushed and hid behind a long drag on his beer. 

Cas rolled his eyes. “You know we were having kinky sex. Why do you even ask?”

Anna snorted and Sam gagged. Jimmy cackled, looking all too pleased with himself. 

“I like it when the Adonis blushes,” Jimmy said between giggles. 

Dean peeked around Cas to stick his tongue out at Jimmy. 

Jimmy fluttered his eyelashes. “Don't tease me, Dean.” 

Cas sighed. “Jimmy, don't be such a dick.”

Jimmy clutched a hand to his chest. “What a thing to say to me...and on my birthday!”

“It's not your birthday,” Cas exclaimed. 

“It could be!” Jimmy yelled in teasing argument. 

“We're twins, jackass. I'd know if it was our birthday!” 

Anna wrapped her arms around her middle as she dissolved into laughter.

“You two are ridiculous,” Dean said with a smile. “And I love it.” 

“I'm glad my annoyance at my brother is amusing to you,” Cas said. 

“Very much so.” Dean nodded. “You should see me and Jo when we get going.”

“Oh please don't,” Sam groaned. 

Anna perked up. “I want to hear this story.” 

“Have you ever heard two people argue about the best way to keep ghosts at bay? For an hour? Because I have.” 

Dean opened his mouth and Sam held up a hand. “Don't even start about salt versus iron because we don't care.” 

Dean closed his mouth into a pout. 

Cas reached down to brush a thumb over his bottom lip. “I wouldn't do that,” he whispered. “You know what that lip does to me.” 

Suddenly a handful of jelly beans crashed down on the couple. Their heads whipped around to find Jimmy pointing a finger at them. 

“No! Bad boys.” Jimmy shook his finger a few times. 

“Whatcha gonna do?” Anna sang softly from her position on the floor. 

Sam choked as he tried to stifle a laugh but only succeeded in making Anna burst into a fit of giggles before laughing himself. 

Dean chuckled and hugged Castiel close. His family was a bunch of misfits, but he wouldn't trade it for the world.


	13. Chapter 13

**Summary for the Chapter:**

> Temperature Play time!

**Notes for the Chapter:**

> Okay, I've never actually partaken in temperature play so if I fucked up majorly PLEASE LET ME KNOW!

Dean sat in the middle of the spare bed atop a blue tarp. His fingers drummed a fast beat against his knee. 

“If you're still unsure we can forgo the activity,” Cas said as he continued setting out materials. 

Dean cleared his throat. “No, I want to. . . I'm just nervous is all.” 

Cas placed the small fire extinguisher within reach and glanced to find Dean's eyes had widened even more. He sighed. “It's a safety precaution, lighting you on fire is not part of the plan.” 

Dean blew out a hard breath. “I know. I know.” 

Cas sat next to him, the tarp crinkling as he shifted. “The candles are specifically for this kind of play. They're low temp so you shouldn't experience more than the recommended discomfort. You've had worse getting spattered with bacon grease.” 

Dean nodded. “Fire just freaks me out.” 

Cas frowned. “Because of your mom?”

Dean's eyes fluttered shut. “Yeah,” he said in a rough voice. 

“Dean,” Cas said gently. “I wouldn't do this if I thought it was unsafe. I wouldn't put your well-being in danger. If you're too uncomfortable, we will stop now.” 

Dean balled his fists on his legs. “I want to. Do it.” 

Cas searched Dean's face for a long moment before nodding. “Safewords.” 

“Green, yellow, red.” 

“When will you call them out?” 

“If I need to slow down and pause or if I want to stop.” Dean's breathing eased a bit when he reminded himself that he had options.

“Lay on your stomach,” Cas instructed. 

Dean obeyed, laying on the small sheet Cas had placed over the scratchy material. He pillowed his head on his arms and turned his face toward his Dom. 

Cas lit the candle and placed it on the table where Dean could keep an eye on the flame easily. He waited a few beats to let the wax melt before picking it back up and blowing out the flame. Where Dean could see, he lifted the candle and tipped it to pour the wax over the inside of his arm. After raising it a bit higher and trying again, he gave a satisfied nod and lit a second candle of the same type. 

Dean focused on the dancing flame, letting his breath deepen with the shifting colors and movement. 

Pinpricks of heat landed on his shoulders, drawing a hiss. Castiel's breath over the area tingled and went straight to Dean's groin. The feeling repeated a few inches down. Again and again, warm wax followed by cool breath pushed Dean toward the endorphin high he'd grown to love. 

He moaned and let his eyes slip shut. 

“Good,” Cas whispered. 

Dimly, Dean heard Cas blow out the second candle and smelled the smoky scent. 

Wax dripped in a straight line down Dean's spine, causing him to arch upward toward it like a cat begging for attention. 

He whimpered softly as another line was poured next to the first.

Dean couldn't see it, but Castiel's smile had turned wicked. He reached for the next implement. . .

Dean gasped as icy cold traced a wet trail alongside the lines of wax. He arched upward toward the feeling, his nerves overcome with sensation. 

He felt warmth as Cas licked where the ice had been. 

Dean's breath came out in soft pants, interrupted only by breathy whimpers. 

Cas kept up the barrage of wax, ice, and tongue; alternating the pattern to keep Dean's nervous system on edge. 

When his sub stopped reacting as quickly, Cas knew he'd reached a limit. Dean's body was so overcome with endorphins it was coloring his ability to feel the sensation properly. Dean wouldn't be able to distinguish pain with enough time to alert Castiel if he went too deep into subspace. 

Cas laid warm, damp cloths over the wax on Dean's back. He rubbed softly to help the wax pull off without hurting Dean's skin. Once it was all removed, he blotted the area dry and applied aloe gel. 

Dean moaned with contentment. 

“Dean? Are you with me?” Cas asked. 

“Nope,” Dean mumbled as he burrowed into his arms. 

Cas chuckled. “How are you feeling?” 

“Good,” Dean sighed. 

“Temperature play is a success?”

“Yup,” Dean replied. “I mean, I'm not so eager to do it again like with the rope but we can put it in the 'things Dean enjoys' category of your little notebook.” 

“Duly noted,” Cas answered. “Sit up.” 

“Juice time!” Dean sang as he pushed into a more upright position. He grinned and took the glass from Castiel's hand. 

“Why don't you go back to our room while I finish cleaning up?” Cas suggested. 

Dean nodded. “Don't be long?” 

Cas kissed him softly. “I won't. Go get comfy.”

“Kay,” Dean said on a yawn. 

True to his word, Cas joined Dean shortly after they parted. He stripped off his clothes so he could join his fiance naked beneath their blankets. 

“Hi,” Dean said as he rolled to curl in Castiel's embrace. 

“Hello, Dean,” Cas sighed, raking his fingers across Dean's scalp.

Dean kissed the skin beneath his mouth. “So, one more kink to go.” 

Cas was silent a moment, fingernails scratching through Dean's hair. “You're still sure about trying it?”

Dean shrugged. “Kind of. I can always safeword out if I don't like it.” 

Cas kissed Dean's forehead. “Very true. Have you decided what pet you would be?”

Dean rubbed his face against Castiel's chest. “I was leaning toward something dog-like for awhile. Now I'm thinking cat.”

“Cat?” Cas raised an eyebrow. “Interesting. Wild or domesticated?”

“A bit of both,” Dean answered, turning his face to hide his blush. 

Cas rubbed a thumb across Dean's pink cheekbone. “You have nothing to be ashamed of, gorgeous. I think you'll make a wonderful cat.” 

“Really?” Dean asked in a sheepish voice. 

“You're intelligent and I always imagined cats would be sassy if they could talk. You enjoy cuddling but only on your own terms; perfect for a previously wild animal.” 

“How do we do this?” 

Cas tapped a finger on Dean's bicep. “Well, I assume you don't want a costume. . .”

Dean's horrified expression had him laughing out loud. “I see I was correct in my assumption. We decide on a period of time for play and go from there. It's another form of roleplay, in my opinion. Only, you're an animal instead of a hot repairman.” 

“How long do we play?” Dean mumbled, slipping into sleep but not wanting to end the conversation yet. 

“We'll start with thirty minutes for your first time. If it's something you want to continue, we can discuss doing it again and for longer.” 

“Mmhmm. Imma sleep now,” Dean said. 

“Love you,” Cas whispered. 

“You too,” Dean whispered back.


	14. Chapter 14

**Summary for the Chapter:**

> Cas raised an eyebrow. “Rough day?” 
> 
> Dean grumbled a response and ran his hands through his hair. “I need it.” 
> 
> Cas nodded. “What do you want?”
> 
> “I want to try the new thing.” 
> 
> Castiel's eyebrows flew upward. “You want to try pet play? Now?”

**Notes for the Chapter:**

> I have never in my life written pet play. Never. This...is so new for me and I'm so fucking proud of how this PORN FREE chapter turned out. Dudes.

Dean's footsteps echoed down the hall as he stomped to the apartment. It had apparently been Douchebag Day at work and every asshole in the area had shown up to get their oil changed. Benny had gotten frustrated and pulled out the Dom voice before he realized what he'd done. Even Garth had been pissy toward the end. 

The door slammed behind him. His jacket hit the floor and he kicked his shoes a few feet away. 

Cas raised an eyebrow. “Rough day?” 

Dean grumbled a response and ran his hands through his hair. “I need it.” 

Cas nodded. “What do you want?”

“I want to try the new thing.” 

Castiel's eyebrows flew upward. “You want to try pet play? Now?”

Dean rubbed his sternum. “It's like a balloon inside my chest, man. It's either something new or something intense.” 

“We'll need to have a discussion first but it can happen.” 

Dean flopped onto the couch, arm going over his face. “Whatever works.” 

“Most find it helpful to establish start and end cues. For instance, I might say, 'Good kitty' to begin and 'Done' to end. We should also set a few basic house rules for the period of play.” 

Dean peeked out from under his forearm. “Rules? We're not playing long.” 

“What if you have to use the restroom during our thirty minutes? Shall I procure a litter box or do you want permission to shift into human for that?” 

Dean blushed. “Ah, got it.” 

“Will you be communicating in animal sounds or something else?” Cas asked. 

Dean frowned. “I hadn't thought of it. I guess cat noises unless it's urgent or I need to safeword.” 

“Fair enough,” Cas answered. “Same safewords?”

Dean nodded. “And 'done' if I need to call it quits early but there's no emergency.” 

Cas smiled, happy to see Dean taking initiative with his own play. “That sounds perfect. Are you ready to begin?”

Dean glanced down at his grubby clothes. “Shower first? Then kitty time?” 

“That will give me time to prep some things as well. Any other boundaries I need to be aware of before we start?” 

Dean chewed his bottom lip. “I don't want to eat off the ground. No bowls or anything. Water is fine; for some reason that doesn't bother me.”

“Understood,” Cas said, standing. He waited for Dean to stand as well before kissing him firmly on the mouth. “I love you. Thank you for sharing this with me.” 

Dean smirked. “Thanks for not making fun of me.” 

Cas rolled his eyes. “Go shower.” 

Dean took his time washing the work grime from his body. A warm feeling of apprehension curled in his gut, but not an ounce of fear. He'd felt similar before the other kinks he'd explored with Cas. 

He held back a chuckle as he pulled lacy white panties up his legs. They hadn't discussed outfit options but panties were always a favorite. 

Dean paused when he walked into the living room. Cas had moved the table and placed several pillows on the floor, a decent sized bowl of water sat near the side of the room, and he could see a small plastic bag from a local pet store on the couch. 

Cas joined him in the hallway and placed a comforting hand on the back of his neck. “Still good? You look so fucking sexy. I can't wait to see that ass swaying as you crawl on the floor.” A muffled growl sounded in his chest. 

“Okay okay, Casanova. Let's do this. You watching the time?” 

Cas nodded. “Would you like to begin on the floor or the couch?”

Dean crossed the room and lowered himself to a pillow, curling his legs underneath himself before resting his upper body against the couch. He quirked an eyebrow at Cas in question. 

Cas nodded. “Good kitty.” 

Dean felt the mental shift happen. He didn't have to worry about the day. The assholes at work didn't matter. He didn't have to make dinner or clean the house. There was no one he had to please or anything. 

He was a cat. Cats gave zero fucks. 

His body relaxed a hair more as Cas settled in on the couch next to him and began petting a hand through his hair. 

Dean nuzzled against Castiel's leg, rubbing forehead and cheekbone against denim. Cas scratching his fingers down Dean's neck and brushed under his jaw. Dean channeled his moan into a purring sound as tingles skated down his throat. 

“I bought you something,” Cas said in a light voice. 

Dean tilted his head and squinted his eyes, the rustle of plastic catching his attention. 

Cas produced a medium sized toy mouse that jingled from an internal bell when shaken. It was bright blue and Dean couldn't suppress the grin that crossed his face. 

Cas dropped it on the floor in front of Dean's pillow, bell jangling as it bounced before settling in place. 

Dean reached out with his fingertips and batted it to one side just to hear the bell again. He did it a few more times before tossing it up in the air. It bounced off Castiel's shoe and skittered a couple of feet away. Dean leaned forward on all fours to smack it back to his space. 

Cas picked it up, causing Dean to grip the edge of his jeans and tug lightly. Cas chuckled and tossed the mouse to the other side of the room. 

Dean pursed his lips before crawling a few paces to where the mouse had fallen. His human brain decided to give Cas a bit of a show. He spread his knees and lowered his upper body to the ground to pick up the mouse with his teeth. He kept the movement slow and controlled so each roll of his muscles showed. 

He crawled back to where Cas sat, head held high and mouse jingling when he tossed his head. He placed the toy on the cushion beside Cas and turned to get a drink of water. 

Again, he spread his knees and pushed his ass back when he lowered toward the ground. He opted to slurp the water instead of licking because, get real, his tongue wasn't designed for drinking from a bowl. 

“Are you hungry?” Cas asked. 

Dean gave his fiance a side-eyed look. They'd discussed no food from the floor. 

Cas patted the spot Dean had vacated and rose. Dean crawled over and settled into position. He took a minute to rub his body against the couch, reveling in the slight scratch from the rough material. 

Cas returned with a plate of shredded chicken and cubes of cheese. He placed the plate on the cushion behind Dean's head. He plucked a piece of chicken between his fingers and offered it to Dean. 

Dean wasn't at all in the mood to eat. 

He decided to let his feelings be known by letting out a confused “meow” before batting the chicken gently to the ground. 

Castiel frowned. “No!” he snapped out. 

Dean flinched and immediately began rubbing his face and head against Castiel's fingers in apology. Cas sighed and scratched beneath his jaw. He got up long enough to move the plate of snacks to the table. 

Cas patted his lap. “Up.” 

Dean obliged, moving up to curl with his head in Castiel's lap. He tucked his legs close to his body and scratched his nails lightly against Castiel's jeans. The scritching sound on the denim was oddly soothing. 

Cas brushed a hand from Dean's head down as far as he could reach across his back and shoulders. Every few pets he'd switch to scratching with his nails. 

Each touch sent sparks across Dean's skin. He wasn't sure what was different, but his nerves were reacting to Castiel's fingers in a way they never had before. 

Cas petted a few more times before rubbing across Dean's cheek. “Done,” he whispered. 

Dean sighed and stretched out his limbs. “Bed to chat?”

Cas nodded. “Sure.” 

“Juice?” Dean asked with a small pout. 

“Cheeky brat. Yes, you can have juice.” 

Dean grinned and skipped to their room. 

Once Cas had settled and Dean had drained his glass, they leaned against the headboard and laced their fingers together. 

“You okay?” Cas asked in a whisper. 

“Yeah,” Dean said, his voice rough. “It was . . . different.”

Cas waited, hoping his silence would give Dean space to formulate a coherent thought. 

“I felt relaxed, you know? But different from subspace. When I go under it's more like I'm being forced to relax by my endorphins. Today I just. . . made the choice. I was a cat. Cats don't worry about anything but what they want at that very moment.”

“Mmhmm,” Castiel hummed. “That makes sense. Anything else?”

“When you touched me it felt different. It was exciting but not in a sexual way. I was just so fucking happy to have your hands on me.” 

“Is it something you'd want to do again?” Cas rubbed a thumb across the back of Dean's hand. 

Dean frowned. “I don't know. I liked it but I'm not ready to jump into being an animal a few nights a week or anything. It did help though. I'm glad we did it.”

“Good.” Cas reached up to cup Dean's face. “You may drop mentally after this so please keep communicating to me. You have to know that I don't think less of you for trying this. I'm very pleased that you trust me enough to attempt something so far outside of the norm. You are strong and I'm so lucky to call you my fiance.”

“I love you,” Dean whispered, pressing their lips together. 

“I love you as well.” 

“Can we go have a beer now?” Dean asked. 

Cas tossed his head back on a laugh. “I am amenable to that decision.”

**Notes for the Chapter:**

> I think we need to get Jimmy and Benny back in the group soon. Who's down for more group play? (with their respective partners)


	15. Chapter 15

**Summary for the Chapter:**

> “Dean,” Cas snapped. “Kneel.” 
> 
> Dean's sub-brain took over and had his body reacting before he could remember to blush for it happening in front of Benny. He shot Cas an icy look. 
> 
> Cas, to his credit, only raised an eyebrow before turning to Benny. “Do you have another leash?”

**Notes for the Chapter:**

> Sorry for the long hiatus. I have many excuses. Most of which involve my depression/anxiety and med adjustments and holiday emotions. 
> 
> But here's a group bit! I think we need some mild angst soon so be on guard. 
> 
> Special note at the end!

Cas rang the bell instead of just letting him and Dean into Benny's. It was weird considering the last several times they'd been there Jimmy had just walked right in, but they didn't feel the same level of comfort. 

Of course, they'd never sucked Benny's cock so it was understandable. 

Benny's booming voice called out, “Come in.” 

Dean and Cas removed their socks and shoes before entering the living room to see the usual scene: Benny on the couch and Jimmy kneeling on the floor. Jimmy, however, was dressed in a pair of tight black shorts and a collar. . . with a leash clipped on. 

He flicked his eyes to the new arrivals before glancing at Benny and back at the floor. 

Dean greeted Benny with a handshake and moved to hug Jimmy. 

“Dean,” Cas said. “Jimmy is observing higher protocol than normal. You may only interact with permission from both of us.” 

He got the expected response.

Dean turned a slow pivot and placed his hands on his hips. “I'm sorry, what? I have to ask permission before saying hello to my friend? You're fucking with me.” 

“Sorry chief,” Benny said with a smirk. “Jimmy's behavior got him in trouble earlier.”

Dean narrowed his eyes and reached for Jimmy again. 

“Dean,” Cas snapped. “Kneel.” 

Dean's sub-brain took over and had his body reacting before he could remember to blush for it happening in front of Benny. He shot Cas an icy look. 

Cas, to his credit, only raised an eyebrow before turning to Benny. “Do you have another leash?” 

“What the fuck?” Dean exclaimed. 

“Perhaps a ball gag as well,” Cas requested. 

Dean snapped his jaws shut with shock. His eyes went wide with fury. 

“Would you like to safeword?” Cas asked in a conversational tone. 

Dean sat back on his feet and considered the question. He was embarrassed, sure, but was it enough to safeword? Was he ashamed of his lifestyle with Cas? No. That wasn't it. 

He swallowed hard as realization dawned. He was embarrassed to have gotten in trouble in front of others. That wasn't a cause for a safeword in Dean's mind; it was a call for apology and acknowledgment. 

“No sir, I'm sorry for my behavior.” Dean directed his eyes at the floor as he removed his jacket. He straightened his posture and gripped his left wrist in his right hand behind his back.

Cas tipped Dean's face up with a finger beneath his chin. “I will forgo the gag if you can watch your mouth, but the leash will help remind you to monitor yourself.” 

Dean nodded, relieved. They hadn't done much in the sense of gags, unless Castiel's cock counted. 

Metal on metal clicked on the circle in front of his throat. He could feel the slight weight as the leash dropped a bit. Cas was right, it did serve as a good reminder. 

He lifted his eyes to see Jimmy looking at him with concern. He shot the dark-haired sub a soft smile and shook his head to indicate he was totally fine. 

Cas tapped the side of Dean's throat. “May I have permission to share our newest experiences with Benny and Jimmy?” 

Dean bit into his bottom lip, flush spreading down his neck and chest. He could see Jimmy's eyes sparkle with glee because a blush meant the details were juicy. 

But if they couldn't talk about it with Benny and Jimmy, who could they talk to?

Dean nodded. “Yes.” 

Cas gave Benny a quick rundown of the new kinks they'd explored along with a brief note as to the success. 

Benny fingered the leash in his hand. “If the boys are up to it, we may have to get our kittens together for a playdate.”

Dean's eyes flew to Jimmy's. Jimmy grinned and sent him a wink. 

“Speaking of rope,” Benny continued. “I got some new stuff in this week. I figured I'd restock if I were going to be playing again. I can pull it out if you two want to use it tonight.” 

A whimper sounded in Deans's throat, causing Cas to chuckle. 

“I think that's a fantastic idea.” Cas raked his fingers through Dean's hair, giving a light tug to pull Dean's head back.

Dean felt the collar bob as he swallowed. His cock swelled rapidly and he shifted his hips. 

Cas smirked. “Let's take this to the playroom, shall we?” 

Benny and Jimmy led the way, giving Cas a moment to pull Dean aside to whisper a quick question. Jimmy glanced back at the soft moan and embarrassed nod from Dean and raised his eyebrows in response. A quick tug on his leash had him moving forward again. 

Jimmy knelt on a pillow in the middle of the playroom, hands clasped behind his neck. The slight arch in his back showed off the lean line of his torso and fully hard cock. 

Dean felt his breath leave him in a rush. Fuck. He was surrounded by intensely hot men. 

Cas stood behind Dean. His long fingers teased at the buttons on Dean's shirt. He slowly popped one after another, stripping his sub for the rest of the room. Harsh breathing and mumbled groans provided background music for the show. 

Dean shrugged his shoulders to help Cas remove his shirt. He shivered as it dragged down his arms and dropped to the floor. 

A jangle announced Cas was working on his belt. He felt the leather whip through the loops in a circle around his waist. The belt sailed through the air as Cas tossed it to Benny with a smirk. Jimmy's mouth dropped open on a silent gasp. He wanted some of that. 

Cas teased a finger along the top of Dean's jeans. Each dip inside caused Dean's hips to twitch in an aborted thrust. 

Benny crossed his arms and watched with an appreciative look. Jimmy's chest heaved as he fought to catch his breath. The arousal in the air was stifling. 

Cas popped the button on Dean's pants before slowly edging the zipper down. He made sure to keep the sides together as he did so. 

Dean tossed his head back and nodded. It seemed to be the cue Cas had waited for because he pulled the sides of Dean's zipper apart to reveal soft pink material. The panties were a sheer satiny material with lace edges. The jeans hit the floor and Dean stepped forward. He turned to kick the pants away and show firm asscheeks peeking out beneath the edge of the lace. Right at his lower back the material was held together with corset style lacing. 

Jimmy's almost pained keen mixed with Benny's deep groan as Dean's muscles bunched and flexed with each movement. 

Benny snapped his fingers and Jimmy hurriedly ripped open the man's pants and sucked down the thick cock inside. Benny raked his fingers through Jimmy's hair with a moan. 

Dean felt the tickle of leather fingers that meant Cas had pulled out a flogger. Pinpricks of sensation rained down on his exposed skin. Blood rushed to the surface. Cas kept each blow moderate. Dean's skin quickly became more sensitive. Cas covered Dean's body, front to back, in beats of leather. 

“Hands behind your head,” Castiel's rough voice demanded. 

Dean, already in an arousal haze, obeyed instantly. He groaned when the wet rasp of Castiel's tongue skated up his spine. Cas dragged his nails up Dean's thighs, feeling the shake in the muscle. 

Dean heard a wet pop and looked over to see Benny pulling his cock from Jimmy's swollen lips. Benny pulled on the leash and guided Jimmy to bend over the bed. 

Cas gave Dean a light shove in that direction. “Sit on the edge, facing me.” 

Dean's ass hit mattress and he waited. 

Cas pulled soft rope Benny had set out between his fingers. Dean's blood heated and scalded in his veins. Fuck yes. 

Cas put a hand out and Dean neatly dropped his wrists into it. The rope weaved in and out into a pair of cuffs tied together. He had Dean wiggle his fingers and rotate his wrists to check the fit before attacking his mouth in a sloppy kiss. 

“Bend over,” Cas growled against Dean's lips. 

Dean flipped so his torso was spread across the bed. His arms stretched over his head and he felt Jimmy's fingers brush against his. He looked up to see Jimmy biting his lip as Benny stroked inside, opening him up. 

The panties were pulled down his legs and tossed toward the rest of his clothes. He could feel the rough denim of Castiel's jeans when the man ground against his ass. 

Cool hands parted heated skin seconds before firm licks overwhelmed Dean's senses. He keened and gasped into the mattress as Cas ate him out. 

It wasn't long before a finger snaked in beside the tongue, stretching the muscle and allowing Castiel to get deeper. 

One finger became two lubed digits and quickly moved to three as Dean's body begged for Castiel's cock. 

“Jimmy?” Cas said in a conversational tone. “Hold him.” 

That was the only warning Dean got before Jimmy's hands pressed on the rope between his wrists as Castiel plunged inside. 

Dean let out a loud cry as he was filled to the hilt and bound in place. His erection was trapped against the mattress and he hoped the friction would be enough to get him off. 

When Cas started moving, he got his answer...

The soft material of the bedspread rubbed the sensitive skin of Dean's cock as his hips moved with each hip snapping thrust from his Dom. 

Benny set a similar pace behind Jimmy. The room filled with cries, groans, and the hard slaps of skin on skin. 

Jimmy babbled in a way that Dean remembered meant he was close to climax. The realization pushed Dean closer to that blissful edge. 

One after the other, each of the four men came on a groan. 

Cas pulled out, causing Dean to whimper softly at the loss. He climbed on the mattress enough to untie the ropes from Dean's wrists. Dean glanced over to see Cas hadn't even gotten undressed. His dick gave a valiant twitch at the mental image. 

Jimmy rubbed the indents on Dean's skin, causing the man to sigh happily. 

Everyone had juice and bites of chocolate after crawling beneath the covers. 

Jimmy pulled Dean close for a brief kiss before rolling to join Benny on the other side of the bed. Dean smiled and shook his head before giving himself to Castiel's embrace.

**Notes for the Chapter:**

> So..I keep getting requests for some Cas/Dean/Jimmy action. I dont' want to turn this fic into that BUT I'm willing to write a one-shot dream sequence ( because Dean's a dirty boy) in the same universe but separate fic file. So those that want to skip it can do so without problems. 
> 
> It will be called "Enter the Sandman" and I'll try to have it up soonish. There will be no Cas/Jimmy action in it (nothing sexual, some mild D/s stuff possibly) I'd recommend subscribing to me as an author if you want to be notified when it hits AO3. If you're interested, give a comment below...it helps encourage me to write.


	16. Chapter 16

CHAPTER SIXTEEN

Jimmy slammed open the door and stalked into the apartment. 

Dean watched as he headed to the fridge and pilfered a beer before draining it in a single go. 

The belch was impressive. 

Cas came out of the bedroom with a confused look on his face. Dean shrugged and shook his head, just as curious. 

“Problem?” Cas asked. 

Jimmy glared. “The fuck you think?” 

“What happened?” Dean inserted before Cas could pull out the Dom voice. 

Jimmy pressed the heels of his hands to his face. “Fucking Benny happened.” 

Dean was up in a flash. “Did he do something?” 

“Nothing that warrants the display of testosterone, but thanks.” 

Cas held up a hand. “Please start over and be sensible this time.” 

Jimmy took a deep breath. “I went to that club where I met your Adonis. I was there for three fucking hours. No one held my interest. No one was going to be good enough.” 

Dean nodded encouragingly and placed a hand on Jimmy's shoulder. 

Jimmy sighed. “So I went to Chains.” 

Dean shot Cas a concerned look and got a slow nod in response. Chains was the bondage club. 

“I thought maybe I was in the mood for a little kink, you know? Maybe the regular club scene wasn't going to be good enough.” His throat tensed as he swallowed. “I kept walking around and watching. But I knew no one would touch me like Benny. I'd never come as hard with any of them. No one would be able to put me in subspace like he can.” 

Dean led Jimmy to the couch. “I don't understand, man. Why is this a bad thing?” 

“Because this isn't me!” Jimmy shouted. “There's a reason I don't fuck the same guy twice.” 

“Benny,” Dean whispered. 

Jimmy curled up on the sofa and put his head in Dean's lap. “I watched our parents fuck up. I watched everyone around me go through the high of love and the low of heartbreak and I swore I'd never let it happen to me. And then you assholes have to come around and be all perfect and shit and part of me starts to want it too.” He shuddered against the urge to sob. “Part of me starts to hope.” 

Cas sat on the floor so he could see his brother's face. “What brought this on? You two were fine when we played the other night.” 

Jimmy swiped at a wayward tear. “He asked me to move in.” 

Dean's heart clenched. “And you said no?” 

“I didn't say anything. I just walked out.” 

As if on cue, Castiel's phone rang. “It's Benny.”

Jimmy fished his phone out of his pocket and tossed it on the floor. “I turned mine off.” 

Castiel growled lowly before answering. “Hello, Benny. Yes he's right here. He's fine. Safe. He'll be staying with me for a few days.” He hung up and pocketed his phone. 

“Most of my shit is at Benny's,” Jimmy mumbled. 

Cas smirked and crossed his arms. “Lucky for you, we're the same size.” 

* * *

The following days were like living with a ghost. 

Cas and Dean saw evidence that Jimmy was still around in the form of dishes in the sink or food disappearing, but rarely did they see the man himself. 

The next weekend, Jimmy woke to scented mist raining down on him. 

“What the hell?” he sputtered as he squirmed until he fell of the bed. “Did you just Febreeze me?”

“You stink,” Dean said, spraying another layer of mist. “Have you showered at all since you got here?” 

Jimmy wrinkled his nose. “What day is it?” 

Dean huffed a frustrated breath and squeezed the sprayer again. 

Jimmy crab walked backwards away. “Pretty sure inhaling it directly is hazardous to my health.” 

“Your current state is hazardous to your health, buddy. Go shower. Get dressed. We're going out.” 

Jimmy coughed. “We?”

“The three of us,” Cas said from the doorway. “You need to get out of the apartment so we're heading to Roadhouse.” 

Jimmy sighed, knowing he wouldn't win in an argument. “Fine.”

“Shower. Fresh clothes. You have twenty minutes.” Cas turned and walked back to their room, Dean following. 

Two hours later found a Jimmy sulking in a corner booth between Castiel and Dean. 

“You two can sit together,” Jimmy grumbled into his beer. 

“No,” Cas, the designated driver, said into his soda. “I don't trust you won't slip out.” 

Jimmy ran light fingers over Dean's forearm. “You trust me beside your Adonis?” 

“I know where you sleep,” was the answer. 

Dean snorted. “Sorry, Ace.” 

Their waitress swept by the table long enough to tell them she had to leave and was handing their care over to someone else. The men acknowledged with a raise of their drinks and smiles. 

Dean had just threatened to throw peanuts at Castiel when a blonde man walked up to their table. 

“Sorry about the fuss, I'm Adam. I'll be taking care of you for the rest of the night.” 

Jimmy licked his lips. “The rest of the night? Is that a promise, Adam?” 

Dean barked a laugh and gave him a shove. “Dude.” 

Adam's eyebrow tilted upward as a slow smirk crossed his face. “Actually, you're my last table. I took over for Mel because she had an emergency. Technically, I was supposed to get off ten minutes ago.” 

Jimmy ran a finger up the side of his glass, collecting condensation. “I'm sorry we impeded your getting off. Maybe I can make it up to you.” 

Dean shot Cas a look across the table. 

Cas rolled his eyes and took another sip of his soda. “Jimmy, I'd like to ask him for another Coke before you put his dick in your mouth.” 

Dean choked on his next drink. 

Jimmy sighed. “Fine.” 

A blushing Adam turned and went to get Cas his refill. 

“You may get his number but you aren't fucking him in the bathroom,” Cas admonished. 

“Why not?” Jimmy whined. 

Cas shook his head. “You are not in the right state of mind. You'll regret it in the morning.” 

“You aren't my Dom,” Jimmy muttered. 

Castiel's hand shot out and gripped Jimmy's chin, turning their faces together. “I may not be your dominant but I am still your brother. And I will haul you bodily out of here and straight to Benny's to sort your shit out if you can't behave.” 

Jimmy's gaze fluttered and he looked down. “I'll behave.” 

Dean shifted in his seat. “Dammit, Cas.” 

“You can wait,” Jimmy laughed. 

Castiel's mouth quirked as he bit back a smile. “He likes to wait actually. In fact...” he signaled Adam to go ahead and close their tab. “Why don't we go dance.” 

“Fuck,” Dean muttered before slamming back the rest of his beer. 

“Somebody's in trouble,” Jimmy sang as they scooted out of the booth. 

“I'll show you trouble,” Dean mumbled. 

Jimmy's knuckles grazed the bulge in Dean's jeans as the two of them made their way to the packed dancefloor. 

Vintage Nelly pulsed through the speakers, declaring it “Hot In Herre” as Dean settled his hands on a gyrating Jimmy. Green eyes met blue in a blaze. 

Dean felt hands at his back and leaned into the embrace without stopping the motion of his hips. He felt nimble fingers skate down the buttons of his overshirt, lighting his skin with sparks despite the tshirt between them. Cas took advantage of the cover of the shirt and dragged fingernails across the skin at the top of Dean's pants. 

Dean groaned, the sound swallowed by the music around them. He fought the urge to shut his eyes in ecstasy. 

He was glad he'd kept his gaze on Jimmy because he got to witness the look of surprise when Adam slid in behind and pressed up to Jimmy's backside. 

The four men continued to move as the temperature between them rose. 

Cas made eye-contact with Jimmy and tilted his head toward the door. Jimmy whispered something in Adam's ear and nodded back to Castiel. 

Cas gripped Dean's hand and began leading him out of the bar. The other men followed behind in silence.

**Notes for the Chapter:**

> I wasn't going to end this here but I wanted to ask....how mad would my readers be if Jimmy slept with someone else at this point in the story?


	17. Chapter 17

**Notes for the Chapter:**

> Short but necessary to set up the next mega chapter. Poll of sorts at the end!

Adam agreed to drive behind as the three men piled into their car. 

Jimmy and Dean pouted in the backseat, having been told not to touch themselves or each other. 

Dean kept shooting little glances at Jimmy, wondering how far he was planning to go with Adam. He and Cas locked eyes in the mirror and Dean could see the curiosity there too. 

Dean took the lead in the walk to the door. Once inside, he was no longer in charge. 

“Couch,” Cas said simply. 

Dean didn't hesitate to comply. He knew they wouldn't be scening with Adam there, but Cas was still calling the shots. 

Dean sank into the couch, spread his thighs, and placed his hands flat on his legs in a waiting position. 

Adam raised an eyebrow but couldn't comment as Jimmy took that moment to bite down on his earlobe before sauntering over to sit next to Dean. 

Adam paused, unsure. He was a guest afterall. Cas decidedly ignored him and instead focused on the gorgeous six feet of submissive waiting to be played with on the sofa. 

Cas stripped to boxers before straddling Dean's lap and attacking his mouth. 

Adam's eyes widened at the display. He looked to Jimmy for a cue. 

Jimmy bit down on his lower lip and moved two fingers in a “come hither” gesture and had Adam's cock standing at attention. Jimmy shifted forward enough to lift Adam's shirt and deliver soft licks and nips to his lower stomach. Adam's hand came out to tangle in Jimmy's hair, causing the dark-haired man to chuckle lowly. 

Jimmy pushed Adam's shirt up and grinned when it was quickly removed. He scratched lightly down the man's thin torso. Shit, he probably should have asked earlier how old the kid was but reasoned he had to be at least 18 to work in a bar...so he was at least legal. 

He made quick work of the button and zip on the boy's jeans, breathing a hot breath on the impressive erection contained within. 

“Commando? At work?” Jimmy teased, looking up at Adam's lust blown eyes. “How deliciously inappropriate.” 

Adam smirked, his eyes raking across Jimmy's face before flicking to the other couple. Cas had Dean's jeans open but still wasn't allowing the sub to touch. If the whimpers were anything to go by, Dean felt tortured. 

Adam's focus returned when Jimmy swallowed his cock down. 

Dean watched those pink lips stretch and licked his lips as he fought to catch his breath. 

Castiel leaned forward. His mouth brushed Dean's ear as he whispered, “My brother has such good ideas.” 

That was the only warning Dean got before he was pressed into the couch and his dick hit the back of Castiel's throat. 

“Oh fuck,” Dean groaned out. He dimly heard Adam's sharp intake of breath at the sight. 

Jimmy shifted their positions lightning fast. Adam's ass had barely hit cushion before Jimmy was sucking him down again. One of Adam's hands buried back in Jimmy's hair while the other shot up to the back of the couch. He watched as both Novak brothers licked and sucked. His balls tightened as the erotic sight pushed him over the edge. 

Adam's sharp cry and huffing breaths combined with Castiel's talented tongue brought Dean to his own edge. “Cas. Please,” he begged between breaths, everything tensing with effort to not come without permission. “Please, sir. May I come?” 

Cas hummed out a pleased note and immediately had to swallow as Dean let go. 

Dean shot Castiel a questioning glance. Cas smirked and shook his head. Fuck. He wasn't done with Dean yet apparently. 

Adam reached shaking hands to Jimmy's belt. Jimmy, however, smiled and gently pushed him away. “I'm good.” 

Adam looked confused. “You're sure?” 

Jimmy nodded. “You should...you should go.” 

“Did I...” Adam began, embarrassment clouding his features. 

Jimmy leaned down and placed a soft kiss on his lips. “You didn't do anything wrong, babe. I just...I realized I can't.” 

Realization crossed Adam's face. “Someone else?” 

Jimmy nodded. 

Adam stood and closed his pants. He pulled on his shirt and enveloped Jimmy in a hug. “Don't fuck up this time.” He rubbed his thumb across Jimmy's swollen lower lip before giving him an understanding smile and exiting the apartment. 

Jimmy closed his eyes for a moment before pivoting back to face the now clothed Dean and Cas. “I need you to take me somewhere.” 

* * * 

Benny sleepily opened the door, wondering who the fuck was ringing the bell at such an insane hour. 

“Jimmy?”

**Notes for the Chapter:**

> Jimmy, obviously, needs to be punished. Who's ready for an intense play session? Of course, Dean and Cas would be there but not playing as hard.


	18. Chapter 18

**Notes for the Chapter:**

> Well hell. I know you were expecting a rough/intense play session here....because SO WAS I. However, it turned into mushy crap. 
> 
> Oh well. I've decided to end this section (not verse *wink*) with one more chapter after this one.

Dean and Cas stood in the driveway outside of Benny's the next night. 

“How mad do you think he was?” Dean asked. 

Cas shook his head. “Jimmy told me Benny put him up in the guest room and then went to work as usual.”

“Dammit, I had today off so I don't know anything.”

Cas wrapped his arms around Dean. “I'm sure it's fine or he wouldn't have invited us over. No one wants witnesses for a homicide.” 

“Maybe we're just supposed to discover the body,” Dean mumbled. 

Castiel rolled his eyes and tugged Dean toward the door. He turned before pressing the bell. “Higher protocol, Dean. Don't make me get the leash.” 

Dean gulped and nodded. He actually didn't mind the leash during a scene but having it used as punishment wasn't as much fun. 

Benny opened the door with a grim expression. “Come on in, guys.” He stopped Dean briefly, “He's fine, chief.” 

Dean's eyes widened but he bit back a retort at an eyebrow raise from Cas. 

The cause for the comment became clear when they got to the living room. 

Jimmy knelt on a large cushion close to the couch wearing nothing but black boxer briefs. His hands were bound behind his back with cuffs clipped together. He wore ankle cuffs connected to a spreader bar between his legs. A ball gag strapped around his face. The ball in between his swollen lips had holes like a wiffle ball and Dean could hear Jimmy's breath huff in and out. 

Castiel's hand came down on the back of Dean's neck. “Breathe out.” 

Air whooshed out of Dean's lungs. 

“Hands,” Cas said next. 

What the...? Dean narrowed his eyes for an instant before he realized his hands were clenched into fists by his sides. 

Benny stood a few feet away with a guarded look on his face. “He said he wanted to be punished.” 

“So you tied him up like cattle?!?” Dean exploded. 

“Dean, kneel.” Cas snapped his fingers and pointed at the carpet. 

Dean's knees hit the floor in automatic response. He pouted up at Castiel with a heated glare. 

“Do you trust Jimmy?” Cas asked. “No words necessary. Shake your head.” 

Dean glared harder before giving a short nod. 

“Do you trust Benny?” 

Dean's eyes flicked over to his friend. He pursed his lips as he fought back angry words before nodding slowly. 

“Then you need to trust that he knows what he's doing.” 

Dean worried his lower lip between his teeth. “I'm sorry.” 

Benny nodded. “Accepted. You're just worried about your friend. It's commendable.” 

Dean raised an eyebrow at Cas, asking permission to speak again. Cas smirked and nodded, gesturing toward Benny. 

“What did Jimmy tell you?” Dean asked. 

Benny let out a frustrated huff. “Nothing. He just kept saying he wanted to be punished.” 

Dean opened his mouth but clicked it shut when a loud growl sounded from Jimmy. He'd pinned Dean with a glare. 

“I think my brother is trying to convey it's not your story to tell,” Castiel said in an amused tone. 

Dean blinked at Jimmy several times before inclining his head to the floor. Fine. 

Benny sighed and gestured toward the playroom before going to unstrap Jimmy. Dean could see the resignation on his face. He wasn't happy about the way things were going. Dean winced. Communication built the foundation of a healthy Dom/sub relationship. Right now, Jimmy had violated that. 

Cas directed Dean to the bed immediately. Once he settled against the headboard, he pulled Dean in to lounge between his legs. 

Dean's stomach sank. If Cas had already decided to pull out the comfort stops, things were going to get ugly. 

Benny unclipped the ball gag from Jimmy's face. The dark-haired sub moved his jaw around to work out the stiffness before dropping to his knees with his head down. 

Dean swore he could feel Castiel's heart break in that second. He felt it too. Brash Jimmy knelt with none of the normal confidence he normally had. Even in his moments of submission anyone could see the playfulness within. All of that was gone. 

Benny crossed his arms. “I'm disappointed in you, cher.” 

“I know,” Jimmy intoned. 

“Stand up. Foot of the bed. Arms up.” 

Dean looked and saw straps leading from the top of each post of the bed seconds before Benny clipped Jimmy to them. Jimmy let his body weight sag a bit before straightening back up. Benny checked the fit before producing a blindfold and covering Jimmy's eyes. 

“Safeword.” 

Jimmy licked his lips. “Green, yellow, red.” 

“I expect you to use them if you need it.” 

Dean could tell by the lines in Jimmy's face that he wasn't planning on it. A quick glance at Benny showed the Dom knew it too. 

Fuck. Fuck. Fuck. 

Dean didn't realize he was moving to get up until Castiel's hands clamped down and pulled him back. “Trust him,” Cas whispered. 

Benny undid his belt, allowing the clank of the buckle to sound more than necessary. 

Jimmy tensed and released, resignation painted across his features. 

He jumped when the belt jangled onto the bed in front of him. 

“Who am I, Jimmy?” 

Jimmy cleared his throat. “Benny, sir.” 

Benny made a clicking noise with his tongue. “Try again.” 

Jimmy pressed his lips together. “My Dominant, sir.” 

Benny ran a gentle hand across Jimmy's shoulders. 

“Please just hurt me. I deserve it.” Jimmy tried to jerk away from the soft touch. 

Benny continued his light exploration of Jimmy's exposed skin. “Do you trust me, Jimmy?” 

Jimmy twitched. “Yes.” 

“I will give you what you need. That doesn't always mean you get what you want.” 

Jimmy made an angry noise and jerked in his bonds. “I need to be punished.” 

“You don't make that decision. From now on, I only want answers to my questions or a safeword. Is that understood?” 

Jimmy chewed his lips in frustration. “Yes, sir.” 

Benny hummed in acknowledgment, gentle hands caressing Jimmy with loving passes. “What happened the other night that brought you to my doorstep?” 

“I sucked someone's dick,” Jimmy spat out. 

Benny only hummed again. There was no anger in his voice when he asked, “So?” 

“What?” 

“So? You made it clear we aren't exclusive. Why should I care you had someone else's cock in your mouth? You enjoy giving head. You have a right to the things you enjoy.” 

Jimmy made a wounded sound. “But...I...”

“Do you want me to be angry?” Benny's hand cupped the side of Jimmy's face. 

Jimmy twisted away from the touch. “Yes.” 

“Why is that?” 

Jimmy twisted and pulled in an effort to escape Benny's closeness. “I don't know!” he shouted. 

“What were you trying to prove to yourself?” 

“No!” Jimmy protested. 

Benny waited in silence. 

“I don't want to need you,” Jimmy whispered. “I can't.” 

Benny moved behind Jimmy, continuing to touch and pet his body. “Do you think that it makes you weak?” 

“It can. It sets me up to hurt. I can't...I won't.” 

Benny hummed. “How do you think it felt to have you walk out on me?” 

Jimmy jolted. “What?” 

“It hurt,” Benny answered. “Because you aren't the only one that needs someone.” 

Jimmy shook his head rapidly. “No,” he whispered. 

Benny stepped in front of his sub. “That's how a relationship works, cher. You're in it together. No one has to be in it alone.” 

Dean sniffed before he realized hot tears were tracking down his face. 

“My guess is,” Benny continued, “that you wanted to prove you didn't need me but it only made it worse. A stranger can satisfy a craving but he can't satiate that need. Because it's different with someone you care about...someone you love.” 

Jimmy choked on a sob. He shook his head again. 

“Shhh,” Benny crooned. “You don't have to say it. I see it when we're together because I feel it too.” 

Jimmy slouched, allowing his bound arms to carry more of his weight as his body was wracked with sobs. 

Benny reached up and pulled the blindfold off. “Let me take care of you,” he whispered. 

Jimmy peered at him through a mass of tears with awe and wonder in his eyes. His mouth parted as if to ask a question before he nodded in silence. 

Benny braced Jimmy before nodding to Cas and Dean to help unclip his wrists. Jimmy all but collapsed in Benny's embrace, tears flooding once more. 

Cas whispered to Benny before gesturing to Dean to head to the door. 

Once the two were back in the Impala and on the road Dean stated, “He didn't spank him.” 

Cas smiled softly. “No. A physical beating is something Jimmy can handle with the utmost stoicism. Being forced to confront his emotions, however....Well, there's a reason the two of you get along so well.” 

Dean huffed in mock offense, even though he knew Cas was right. “So what now?” 

“I expect lots of talking will be involved but I believe they made a breakthrough tonight.” 

Dean reached out and laced their hands together. “I love you.” 

Cas squeezed his fiance's hand. “And I you.”


	19. Epilogue

**Notes for the Chapter:**

> The final bit to close out this piece of the story and open the next door. More in the end-notes.

“Anna!” Dean called from her kitchen. “Where's the whiskey?” 

Everyone had finally gotten together at Anna and Charlie's place for an evening. The petite redhead computer nerd fit right in and immediately bonded with Dean over a love of Star Wars. 

“I'll help you,” Cas said as he entered the room.

Dean spun to place his backside against the counter. “You stay right there. Just point.” 

A feral smirk crossed Castiel's face. “What's the matter, baby?” He steadily advanced on Dean. 

Dean whimpered and scooted sideways. He'd mouthed off a few hours prior to their departure and earned himself a paddling. His ass still stung. 

Cas pressed their bodies together, trapping Dean against the cabinet. He reached around to grab a handful of his sub's ass. “Sore?” 

Dean tried to glare even though his body responded by rutting against Cas. 

Movement in the doorway caught Dean's attention. “Jimmy, how long have you been standing there?” 

The twin grinned. “Longer than you'd like. The whiskey is over there by the way.” He pointed to a cabinet on the other side of the room. 

“Thank you, JIMMY.” Dean said, sending a mock glare at his fiance. He retrieved the bottle and gestured for Castiel to go first. 

The trio entered the room as Charlie wrapped up a story in a giggly voice. “...and that was the day everyone learned not to mess with Unicorn Boy.”

Sam and Jo laughed until tears tracked down their faces and they gasped for breath. Benny shook his head in amusement and reached to pull Jimmy into his lap. 

Anna scooted over and patted the floor next to her. “Sit with me, Dean.” 

Dean shook his head. “Thanks, I'll stand.” 

Charlie smiled. “Someone got in trouble,” she sang as she took a sip of her drink. 

Jo's eyes twinkled. “Did someone get a spanking?” 

“Shut up,” Dean mumbled. 

Sam looked pained. “Really, please do shut up.” 

Jimmy licked his lips. “What's wrong, Moose? Don't like thinking about your big brother all bent over and . . .” 

Benny's hand clamped down on Jimmy's mouth. “I brought the ball-gag, cher.” 

Jimmy's eyes widened and he wiggled in place. 

“It's not a good threat if he likes it,” Jo pointed out. 

Benny nodded. “True. Jimmy, you be nice to Dean and Sam or no sex for a week.” 

Jimmy swallowed hard before nodding seriously. “Sorry, Adonis. Sorry, Moose.” 

Jo snorted. “Moose, Adonis. Why don't I get a fun nickname?” 

Jimmy shrugged. “I haven't come up with yours yet.” 

“He just calls me Red,” Charlie said. “Better to wait until his creative juices get going.” 

“Barbie?” Jimmy tried out. 

Jo's eyes narrowed. “I will cut you with the knife in my boot.” 

Jimmy put his hands up. “I'll keep thinking. Jeeze.” 

Anna pulled a cushion from the back of the sofa and set it on the floor. Dean smiled gratefully before settling in. 

No sooner had his ass hit the pillow, the doorbell rang. 

Everyone glanced around with confused looks on their faces. Anna and Charlie had a silent “did you invite someone” conversation that ended in both women indicating the negative. 

Sam, the largest of the group and therefore most imposing, elected himself to answer the door. 

The rest of the crowd sat with bated breath as the sound of the door opening cut through the room. 

“Well, aren't you massive. I hope you're not the groom. Well, the other groom. I heard something about a wedding.” 

Jimmy, Anna, and Cas each exclaimed “GABRIEL” in amusement, confusion, and a groan.

**Notes for the Chapter:**

> I'm going to continue this, but slowly. My current medication inhibits a lot of my creativity so it comes in fits instead of a constant flow. It's been 6 months and I'm still adjusting and learning. 
> 
> If you're reading "Once Upon A Winchester" have no fear, it's not abandoned either...just slow going. 
> 
> So the next story will be wedding planning....considering I eloped, I have no idea what I'm doing. I'm also going to include all the kinks again so be sure and comment with your favorites down below. 
> 
> Thank you so much for sticking with me!


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